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Being a tourist in Portland, Maine is simple; the city is compact and easy to walk around. The charms of Portland also make being a tourist here an easy task. Locals love it here and of course know all the best hidden spots. We lived here for 14 years only to leave in 2017 to travel full time – we know plenty of these secret haunts and you certainly need an insiders edge during your visit to find them. So, enjoy Portland like a local – as a tourist.

Vintage postcard saying greetings from Portland, Maine

Portland, Maine has made many “top 10” lists for quite a while now with it’s most recent accolade coming from “Bon Appétit” magazine earlier in 2018. What was once a run-of-the-mill coastal town with a working waterfront has now become a highly desirable relocation investment for many –  both commercial and residential.

A row of Victorian brick brick buildings

The city whose working waterfront sustained it for so long has developed a hip alter ego, with galleries, boutique hotels, world-class restaurants, cute cafés, local distilleries and a thriving craft brewery scene.

Local Haunts

Rather than present you with another list of must-see lighthouses, best places to get a lobster roll or fabbest new foodie find, we reckoned we’d give you a tour from a local’s perspective.

Whether you only have 24 hours in Portland, Maine or you’re flush with time, we have a suggestion for all seasons and then some. So, wander with us through downtown Portland and we’ll take you to our favourite spots in the outlying neighbourhoods.

A row of colorfully painted apartment buildings

We feature the best least known places tourists are seldom aware of. Order Disco Chicken then boogie the night away on a light-up dance floor! Build a fairy house in a fairy village on an island. Prove your cerebral fitness at a neighbouhood pub and win a free beer. Visiting Portland, Maine in Winter? Whatever the season or reason we’ll show you how to enjoy Portland like a local – as a tourist!

The order of this post is by category. The categories are:

  • Food & Drink 
  • Bakeries
  • Shopping
  • Get Out Now! 
  • Pack a Picnic
  • Entertainment
  • Art, Street Art and a Bit of History
  • Seasonal

But first…


Need More Info?

Fancy a more in depth view of what Portland and New England have to offer? Click on the books below to find out how to get your own comprehensive travel guide. Lonely Planet has been one of the top go-to guides for travellers for more than 40 years!

Eastern USA Lonely Planet book.

New England Lonely Planet book.

New Englands Best Trips Lonely Planet book.

 


Getting To, From and Around

Arriving to and moving on from Portland couldn’t be easier. The airport is only minutes from town and the bus and train station is even closer.


By Air

Portland International Jetport (PWM) is located just 3.5 miles from the center of town, making public transport to and from the airport a breeze. Portland’s METRO bus operates a route to downtown from the Jetport – look for the bus stop directly outside baggage claim. For information on the airport route, click here. For more information on the METRO, see below.

Bd2media, Pwm jetport term, CC BY-SA 4.0

City Bus

The Greater Portland METRO operates multiple routes within the city and to a select few surrounding suburbs; getting around town during your visit couldn’t be easier. For more information on Portland’s METRO bus service, fares and schedules, click here.

Long Distance Bus and Train Service

The Portland Transportation Center handles trains and buses to and from Portland, Maine to Boston’s South Station. In addition, bus service from Portland Transportation Center includes routes to and from Portland, Maine to Boston’s Logan International Airport, New York City, New Hampshire and Bangor, Maine. Note: All bus routes to and from Portland Transportation Center are operated by the same carrier, Concord Coach Lines.

Discount carrier Megabus offers routes to Boston, operated by Concord Coach Lines – check the Megabus website for more information. Trains to Boston are aboard the Amtrak Downeaster.

  • Train: For Amtrak Downeaster schedules and fares between Portland, Maine and Boston click here.
  • Bus: For bus schedules and fares from Portland, Maine to Boston’s South Station and Logan Airport and other routes, click here.

Amtrak train

Greyhound Bus

Finally, less frequent Greyhound bus service operates from a small corner terminal about a half mile from the Portland Transportation Center. For the location of the Greyhound terminal in Portland, Maine, schedules, fares and destinations, click here.

Greyhound logo painted on the side of Pizza Villa in Portland, Maine


Food & Drink

Denizens of Portland certainly have their favorite bars and restaurants; follow one during your visit and find out where they go!


The Bayou Kitchen

Where: 543 Deering Ave. Portland, Maine 04103

Hours: 

  • Mon. – Sat. 7:00 am – 2:00 pm
  • Sun. 8:00 am – 2:00 pm

Telephone:  (207) 774 4935

Website: www.thebayoukitchenmaine.com

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Looking for one of the best breakfast places Portland, Maine has to offer? Step away from the peninsula and head to the Woodfords neighborhood in search of true flavor. The Bayou Kitchen occupies an old building in a confidently cool, up-and-coming part of town. This is the original Cajun restaurant in Portland and a true local favorite. Get here early during the weekend; this place fills up quick.

Colorful shopfront of The Bayou Kitchen in Portland, Maine.
Photo Courtesy of The Bayou Kitchen

The Bayou Kitchen menu features serious Cajun flavor and specialties that’ll pleasantly pep up your morning. For example, order the andouille sausage or tender crawfish tail meat as extra fixins to jazz up your omelet. Keep the heat going with a piece of Jalapeño & Cheddar cornbread.

If spice isn’t for you, the Bayou Kitchen menu also features tamer breakfast offerings such as French toast, grits, corned beef hash and some of the best pancakes in Portland. The homies (home fries) at Bayou Kitchen are legendary! The Mudbug Madness, an omelet featuring crawfish tail meat, definitely comes with a strong Drifters Recommendation.

Speaking of spice, check out Bayou Kitchen’s wall of hot sauces featuring our favorite Maine made concoction, Lost Woods Hot Sauce. Bottles are available for purchase; taste a few with breakfast and pick a winner to take home. The devotion to flavor and spice at the Bayou Kitchen comes thorough quite nicely with their fresh, homemade salsa; don’t leave town without trying it.

Interior of the Bayou Kitchen restaurant in Portland, Maine.
Photo Courtesy of The Bayou Kitchen

The Bayou Kitchen menu lets you spice up lunch too, with Chicken Piquant soup, Chicken and Sausage Gumbo or deep-flavored Classic or Veggie Jambalaya. Expertly grilled burgers, either basic or pepped up with fiery fixins, are available on weekdays only. Just as legendary as the home fries at Bayou Kitchen is the spicy beef chili at Bayou Kitchen, available without beans for the picky eaters in your group.


Susan’s Fish-n-Chips

Where1135 Forest Ave. Portland, Maine 04103

Hours: Daily 11:00 am – 8:00 pm

Telephone: (207) 878 3240

Website: www.susansfishnchips.com

Get caught up in the fun nautical decor and enjoy a variety of fine fried seafood at Susan’s Fish-n-Chips. Try their famous fried lobster tail on a stick (this is Maine) for something truly unique. The menu at Susan’s Fish-n-Chips even includes fried trout. Simply put, locals have been coming here for nearly 30 years for some of the best fish and chips and hand cut onion rings in Portland!

plate of fish and chips with a side of coleslaw
Photo Courtesy of Susan’s Fish-n-Chips

The menu goes beyond fried fillets of fish, offering battered calamari, clams and our favorites – fried oysters and scallops! Every Monday and Tuesday enjoy Susan’s Fish-n-Chips famous special – 2 fish burgers for $2.50, all day long! For landlubbers not interested in seafood, Susan’s Fish-n-Chips menu features hamburgers, cheeseburgers and hot dogs.

Lobster tail on a stick from Susan's Fish n Chips in Portland, Maine.
Lobster Tail on a Stick. Photo Courtesy of Susan’s Fish-n-Chips
a tray full of cups of colesla
The Best Coleslaw in the World. Photo Courtesy of Susan’s Fish-n-Chips

Don’t miss Susan’s Fish-n-Chips homemade coleslaw – the best you will find anywhere. At $1.99 per tub, Susan’s coleslaw is available to-go if you’re heading to the mountains and lakes during your visit to Portland. So pack a picnic for that day trip and bring some coleslaw from Susan’s Fish-n-Chips!


Where: 540 Forest Ave. Portland, Maine 04103

Hours: Daily 11:30 am – 11:30 pm

Telephone: (207) 772 0300

Website: www.greatlostbear.com

It seems all of Portland loves this neighborhood beer mecca. With over 70 rotating taps featuring microbrews from Maine and beyond, Great Lost Bear offers a pint or flight for any taste. However, we love the Great Lost Bear for keeping it real with $1.99 pounders of Schlitz for traditional brew lovers.

The cozy atmosphere at the Great Lost Bear – neon signs, antique photographs, vintage beer memorabilia and assorted ephemera – certainly makes this a great choice for a pint on a rainy day. That same warm atmosphere is the perfect remedy for Portland, Maine in Winter.

colorful mural for The Great Lost Bear in Portland, Maine on the side of a brick building.
Support Your Right to Arm Bears!

The Great Lost Bear has a huge menu filled with uniquely named dishes. Try not to laugh as you order the Almighty Cheesus Burger or the Mother and Child Reunion (fried chicken and fried egg), for example. The funny sounding dishes here will not prepare you for the serious portions served here – consider yourself warned. Order some of the best burgers in Portland, Maine and pair them with a microbrew from the almost world-famous Great Lost Bear Beer Menu.

Finally, don’t leave the Great Lost Bear without trying to win a free beer by answering the daily trivia question posted on the blackboard behind the bar. The Great Lost Bear is a fun place to be and makes a great choice for a meal. Pop in for some cheer during your visit – this is one of the best pubs in Portland, Maine!


The Jewel Box

Where: 644 Congress Street, Portland, Maine

Hours: Daily 5:00 pm – 1:00 am

Telephone: (207) 747 5384

Website: www.jewelboxportlandmaine.com

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Monthly Rotating Cocktail Menu on Instagram

Described by some as a speakeasy, this intimate cocktail bar does have a sign, you just have to look for it. The subtle signage allows the “Jewel Box” to hide in plain sight in the Arts District of Downtown Portland. The mystique of locating this wee gem adds to it’s allure.

Photo of the famous mural at the Jewel Box cocktail lounge in Portland, Maine.
Photo Courtesy of Nathaniel Meiklejohn

Once inside it is evident the raison d’être of this hipster hideaway is the cocktail menu. It is possible to grab a beer or a glass of wine here too, but this is not your typical bar so do not expect an extensive beer and wine list.

interior of the Jewel Box cocktail lounge in Portland, Maine.
Photo Courtesy of Nathaniel Meiklejohn

The primary focus here is the unique monthly revolving cocktail menu, crafted by the in-house mixologists. Standard spirits are given a makeover – infused with bitters, liqueurs, fresh fruit and fruit juices, creating one of a kind concoctions with equally idiosyncratic names. If you are peckish there is also a small tapas menu.

Photo of interior of Jewel Box cocktail lounge in Portland, Maine.
Photo Courtesy of Nathaniel Meiklejohn

Grab a seat at the bar and learn a thing or two about mixing your drinks. Alternatively, head upstairs and cozy up on one of the loveseats for a more intimate ambiance, especially if you arrive early in the evening.

The decor throughout is a mixture of retro chic, offset with vintage glassware and antique accent pieces. From the ceiling hang veils of gossamer, whilst the glow of candlelight suffuses the “Jewel Box” with the mellow warmth of a welcome retreat. Raise a glass of spirits and feel your spirits rise in this elegant, affable locals favourite.


Silly’s

Where: 40 Washington Ave. Portland, Maine 04101

Hours:

  • Wed. –  Fri. 11:00 am – 9:00 pm
  • Sat. – Sun. 9:00 am – 9:00 pm
  • Closed Mon. & Tue.

Telephone: (207) 772 0360

Website: www.sillys.com

Silly’s pulls no punches with their menu, featuring a rather vast selection of wraps, sandwiches, burgers and pizzas. Silly’s menu even features enough vegan and vegetarian choices to keep everyone in your group smiling. There is certainly nothing nonsensical about their commitment to those with dietary needs and restrictions – Silly’s uses a dedicated fryer for vegans and even a gluten free fryer.

Front window at Silly's Restaurant in Portland, Maine.
Photo Courtesy of Silly’s

The whimsical theme here is evident all around as you walk through the door and continues as you browse the menu. Each item on Silly’s menu is given a clever moniker such as One Foot in the Gravy, Thai One On, or Put Me in the Game, Poach! This encourages you to read what each offering consists of rather than just recognizing it by name. That’s a good thing because the creations and flavors at Silly’s have been given some serious thought and feature truly unique flavor combinations.

The Famous Leg Lamp at Silly's Restaurant in Portland, Maine.
Photo Courtesy of Silly’s
bumper sticker from Silly's Restaurant in Portland, Maine.
Photo Courtesy of Silly’s

This is fresh, minimally processed food prepared with serious passion. In fact, the only foods Silly’s doesn’t make, according to their website, are the tortillas and ketchup. Locals who’ve been coming here for over 30 years, along with plenty of devotees from afar, are featured in photos throughout the restaurant proudly brandishing a Silly’s bumper sticker in famous locations throughout the world. Click here to see a few of these rather sincere Silly’s supporters.


Bubba’s Sulky Lounge

Where: 92 Portland Street, Portland, Maine 04101

Hours:

  • Sun. – Thurs. 8:00 am – 7:00 pm
  • Fri. & Sat. 8:00 am – 1:00 am

  • Fri. “80’s Night” 8:30 pm – 1:00 am
  • Sat. “Everything Dance Party” 9:00 pm – 1:00 am 

Telephone: (207) 828 0549

Website: www.bubbassulkylounge.com

Note: Bubba’s Sulky Lounge Is Cash Only!

A visit to Portland is not complete without grabbing an afternoon beer at “Bubba’s”. Words cannot do justice to describe this cherished Portland institution. Kooky, bizarre, kitsch, funky, quirky, weird, strange, vintage and dive bar are just a few of the common adjectives used in connection with Bubba’s. This was always a “must visit” place we took out-of-town guests to.

Grab a swivel lounge chair at the bar or sit in one of the booths. That is if you can make it to the bar without being distracted by the life-size dioramas complete with mannequins and antique fixtures. The bar chairs won’t be the only thing swivelling at Bubba’s, your head will swivel as you marvel at the hundreds of vintage metal lunch boxes above your head strung across the ceiling.

If you’ve ever wondered How Deep is Your Love for an authentic 70’s light-up dance floor, then You Should Be Dancing at Bubba’s on Friday and Saturday nights. No, the Bee Gees reference is no coincidence here – you really can show off your best Saturday Night Fever moves to the perfectly synchronised, illuminated, pulsating beat of the light-up dance floor. Bubba’s in Portland, Maine is both a trip and a trip down memory lane.


Vientiane Market

Where: 157 Noyes St. Portland, Maine 04103

Hours: 

  • Mon. – Sat. 10:30 am – 9:00 pm
  • Closed Sun.

Telephone: (207) 774 7311 OR (207) 879 1614

Website: www.vientianemarket.net

We lived around the corner from Vientiane Market in Portland’s Oakdale neighborhood. During our 14 years in the city we visited this tiny corner market often and swear by the food here. It seems all of Portland – firefighters, police, paramedics, local celebrities and politicians –  would certainly agree with us. Don’t let the Asian grocery store appearance fool you – Vientiane Market specializes in fresh cooked Thai food.

Pad Thai is represented well here but try the overlooked Yum Nua instead for a truly light and flavorful dish or the rich Bangkok chicken, cooked in a pineapple curry sauce. In conclusion, Vientiane serves some of the best Thai in Portland, Maine – according to the locals, anyway. Enjoy your meal at one of the several tables provided or order it to go.

NOTE: Vientiane Market uses a “star” system when taking your order: 0 stars mean no spice and 5 stars mean full spice. Be prepared for a concerned warning from staff if you opt for anything above 3 stars!


Downtown Lounge

Where: 606 Congress St. Portland, Maine 04101

Hours: Daily 5:00 pm – 1:00 am

Happy Hour: Daily 5:00 pm – 7:00 pm

Telephone: (207) 773 1363

Step inside this long narrow bar and enjoy a drink in a down-to-earth, no frills local’s hangout. Seating is limited to sitting at the bar or grabbing a booth along the wall opposite the bar. A blackboard above the booths highlights the day’s menu.

Oft described as Portland’s quintessential dive bar, the DTL as it is affectionately known by locals, is everything a dive bar should be. The dim lighting and bordello red walls create an inviting, cozy respite from life beyond these confines. Perfect for an early evening pint alone or a place to get together with friends.

Located across from the State Theatre and smack dab in the middle of the Arts District, the Downtown Lounge is conveniently en route of your First Friday Art Walk. It is also renowned in local circles as Portland’s best Happy Hour.

As the night wears on and your bladder expands, let a trip to the toilets be your gauge on calling it a night. With 3 or 4 narrow steps to climb to make it to the loo, this is the ultimate intoxication indicator!


Bakeries

From rustic breads to pastries and pies, these bakeries in Portland, Maine deserve a category all their own.


Two Fat Cats Bakery

Where: 47 India St. #D, Portland, Maine 04101

Hours:

  • Tues. – Sat. 8:00 am – 5:00 pm
  • Sun. 8:00 am – 4:00 pm
  • Closed Mon.

Telephone: (207) 347 5144

Website: www.twofatcatsbakery.com

Looking for a sweet treat bakery in Portland, Maine? Every now and then it is good to succumb to your sweet tooth and Two Fat Cats Bakery is the place to indulge those cravings. If you’ve never been to Maine before, now is your chance to try the official state treat – the whoopie pie. Two Fat Cats is the place for the best cakes in Portland, Maine.

Whoopie Pies on a table at Two Fat Cats Bakery in Portland, Maine.
Whoopie Pies. Photo Courtesy of Two Fat Cats Bakery

As for our own personal recommendations, you can never go wrong with a chocolate cupcake or a good old reliable chocolate chip cookie. If you are in need of a cake for a special occasion this Drifter’s Recommendation is the Fat Cat Lemon, found under specialty cakes on their website. So deliciously light and lemony, it’s easy to “unintentionally” down a couple of slices in one sitting.


Standard Baking Co.

Where: 75 Commercial St. Portland, Maine 04101

Hours:

  • Mon. – Fri. 7:00 am – 6:00 pm
  • Sat. and Sun. 7:00 am – 5:00 pm

Telephone: (207) 773 2112

Website: www.standardbakingco.com

Alright, so this is definitely not a hidden gem but it is still a gem. In Summer there are queues out the door in the morning-time. In Winter locals reclaim this sweet little bakery for themselves without having to jostle with the out-of-towners.

The Standard Baking Co. in Portland, Maine.

What’s good here? Everything is, but we want to highlight our favourite bread at Standard Baking Co. Whether you’re going on a picnic or perhaps just fancy some of the best crusty bread around, pick up a loaf of stirato at one of the best bakeries in Portland, Maine. Crusty on the outside and slightly chewy on the inside, this is as close as you can get to perfection. Standard Baking Co. have perfected the art of real bread making stateside.


Shopping

Go home with a truly unique reminder of your visit to Portland or just have fun browsing with the locals at the market.


Strange Maine

Where: 578 Congress St. Portland, Maine 04101

Hours: Daily 11:00 am – 7:00 pm

Phone: (207) 771 9997

Website: www.kraag.org/strange

What’s in a name? In this case everything! If you are looking for quirky, bizarre, random, kitsch – and that’s just the decor of this tiny little local curio, then look no further. Every inch and corner of Strange Maine’s downtown shop is full of stuff to keep you engaged.

Shop front of Strange Maine in Portland, Maine.
Photo Courtesy of Brendan Evans

Action figures from your days of youth hang from the walls and ceiling. A few vintage board games are stacked near a collection of VHS tapes with titles we’d love to forget but can’t. Shelves of kooky books and old video game cartridges seem to close in on you as ephemera, outlandish artwork and whimsical drawings drip from every surface.

Take your time and have a blast browsing this boutique of the bizarre – you are guaranteed to find something to make you smile. Although Strange Maine is perfectly normal turf for local collectors and aficionados of vintage media (CDs, cassettes, 8-tracks and vinyl) and pastimes, you just may walk out yourself with a Pet Rock or a Stretch Armstrong toy accompanying you. Come here at once for your next pleasantly strange experience!


Material Objects

Where: 500 Congress St. Portland, Maine 04101

Hours:

  • Mon. – Sat. 10:00 am – 6:00 pm
  • Sun. 11:00 am – 5:00 pm

Telephone: (207) 774 1241

Website: For details, check out Material Objects on Facebook.

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This little consignment shop sells men’s and women’s clothing, shoes, jewelry and accessories. Whether you’re looking for vintage, new or used, Material Objects has you covered.

With almost 40 years of business behind them (since 1979), they’ve seen plenty of fashion trends come and go. Like so many things fashion is cyclical but Material Objects is there to give a new lease of life to wardrobes of yesteryear and yesterday.

Whether you’re looking for classic elegance, funky throwbacks, everyday wear with a dash of flair, classy ensembles, chic individuality or a cozy cape to keep that Maine Winter cold at bay, Material Objects is your only go to. Don’t believe me, see for yourself on their Instagram feed.

Photo Courtesy of Material Objects
Photo Courtesy of Material Objects

Hidden amongst the racks you may well find that one of a kind kit that has been eluding you at all the other clothes shops. Not only will you find unique, hip, quality threads but you do not need deep pockets to shop here either.


Portland Architectural Salvage

Where: 131 Preble St. Portland, Maine 04101

Hours: See website below for current hours.

Phone: (207) 780 0634

Website: www.portlandsalvage.com

Spend hours at Portland Architectural Salvage exploring multiple floors of grand old fixtures, stained glass panels, solid wood doors, fireplace mantles, windows and other assorted house parts.

This rather unique 20,000 sq. ft. antique shop specializes in embracing the quality, character and true craftsmanship of a time gone-by. The atmospheric old showroom, itself located in an old salvaged mattress factory, is well worth your time during a visit to Portland.

Fortunately, Portland has a great stock of old homes. Unfortunately, people update (ruin) the soul of these homes. Fortunately, Portland Architectural Salvage insists the spirit live on by providing these cast-off wares to renovators who agree.

Intricately carved wood moldings, solid, well-built furniture and fancy ironwork were once standard things in many homes. Now, they exist here and blend in quite well among the worn hardwood floors and chunky timber beams of this magical showroom. Portland Architectural Salvage is certainly one of the most unique antique stores in Portland, Maine.


Portland Farmers Markets

When & Where:

  • End of April – November: Sat. 7:00 am – 1:00 pm, Deering Oaks Park, Portland, Maine.
  • May – November: Wed. 7:00 am – 1:00 pm, Monument Square, Portland, Maine.
  • December – mid April: Sat. 9:00 am – 1:00 pm,  631 Stephens Ave. Portland, Maine.

For a map of these locations click here

Website: www.portlandmainefarmersmarket.org

Everyone loves farmers markets and locals here love theirs all year-long! Even Portland, Maine in winter cannot stop the market activity and folks couldn’t be happier. During winter months the market (mercifully) moves to an indoor location in the Deering neighborhood. During spring and summer months the market moves to Deering Oaks Park, offering a pleasant outdoor setting in the middle of the city.

The seasonal Wednesday market on Monument Square, the heart of downtown, offers plenty of atmosphere and local products. Although you can’t cook cauliflower in your hotel room, you can find plenty of local-made foods (hot sauces, honey, jams, etc.) to bring home as a souvenir. Check out the local offerings during your visit!


Get Out! Now! 

Craving some fresh air and a bit of exercise? You don’t have to go far in Portland to find a wooded park or trail.


Evergreen Cemetery

Where: 672 Stevens Ave. Portland, Maine 04103

Hours: Daily, 8:00 am – 4:30 pm

Phone: (207) 808 5452

Website: www.portlandmaine.gov

A National Historic Landmark, Evergreen Cemetery in Portland, Maine features over 230 acres of wooded grounds, wetlands, springs and old carriage paths. Modeled after Mount Auburn Cemetery in Cambridge, Massachusetts this garden-style cemetery is a rather peaceful place to walk, jog or ride a bike.

As you enter the cemetery, the din of traffic soon disappears and forest quickly surrounds this park-like space. Visiting Portland, Maine in winter? Evergreen Cemetery is a great place to snowshoe and cross-country ski. Evergreen Cemetery is also a great place to come for autumn leaf peeping in a somber, yet oddly appealing location.

Autumn trees at Evergreen Cemetery in Portland, Maine.

In short, Evergreen Cemetery is the best place in Portland, Maine to enjoy both spring and autumn foliage. Staying in town and you haven’t a car? Take the Metro from the Pulse downtown! Routes 9A and 9B (in PDF) drop you in front of Evergreen Cemetery.


Standpipe Park or Sumner Park or Top of the World Park

Where: North St. between Quebec and Melbourne Sts. in Portland’s Munjoy Hill neighborhood.

Looking for Portland skyline photo locations? This is it! Google Maps shows this vantage point as Top of the World Park, located within Sumner Park. To confuse matters, locals refer to this location as Standpipe ParkMultiple names aside, all locals agree this is the best view of the Portland, Maine skyline.

View of Portland, Maine from Standpipe Park.

A simple path leads through this acre-sized park to 4 wooden benches overlooking downtown, the Back Cove and beyond –  come here for that ultimate Portland selfie, then take a seat to ponder, plan and peruse the best view of the Portland skyline from this perfectly placed perch.


Portland Trails

Website: www.trails.org

Did you know there is a great network of over 70 miles of wooded and urban trails in and around Portland? As a result these trails offer an astounding variety of sights, terrain, backdrops and skill levels.

From Jewell Falls, Portland’s only waterfall, to a harbor walk book-ended by a beach and a lighthouse, these trails are a great resource for locals (and tourists!) all year. Get out and stretch those legs during your stay!

A sign for Baxter Woods Park in Portland, Maine surrounded by tress and snow
Part of Portland Trails

Looking for bike trails in Portland, Maine? There are plenty of mixed-use trails throughout the city to choose from. If you left your other ride at home visit the enCYCLEpedia or Gorham Bike and Ski for the best bike rentals in Portland, Maine.

For an interactive trail map, click here. For a classic map and information on each trail, click here. Visit their website above to learn more about this nonprofit urban land trust. Get out and enjoy miles of hiking in Portland and some of the best paved bike trails in Maine!


Mackworth Island State Park

Where: Andrews Ave. Falmouth, Maine 04105. Take US Route 1 north from Portland, follow signs for Mackworth Island – the island is connected to the mainland by a causeway.

Admission Fee: Adult Maine Resident: $3. Adult Non Resident: $4. Senior Non Resident: $1.

Websitewww.visitmaine.com

This 100-acre wooded island has a rather dark history surrounding the Governor Baxter School For The Deaf. Today however, locals stroll the trail around Mackworth Island to take in fine views of Casco Bay and Fort Gorges. Former Maine Governor Percival Baxter once maintained a residence on the island, deeding it to the state in 1943.

fairy house against a tree, built from tiny wood planks and stones on Mackworth Island in Portland/Falmouth, Maine
A Fairy House

Follow a rather easy, 1.25 mile circuitous footpath around Mackworth Island and enjoy a few quirky sights along the way. For example, Governor Baxter’s pet cemetery is off the trail, as is a small pine grove where you’ll find the fairy village of Mackworth Island. Above all, do not leave the island without constructing a fairy house for these tiny forest dwellers – it’s bad luck.


Winter Activities at Riverside Golf Course

Where: 1158 Riverside St. Portland, Maine 04103

Hours: 24 hours a day/7 days a week – in winter months only!

Admission Charge: FREE!!

Website: www.riversidegolfcourseme.com

Visiting Portland, Maine in winter? Celebrate all things cold and snowy at Riverside Golf Course during your stay! This municipal golf course turns into an all-purpose winter playground as soon as the snow flies. In winter the entire course is open 24/7 and provides free access to sledding hills, cross-country skiing trails, snowshoeing paths, an ice skating rink and acres of fat tire biking trails!

Sled hill at riverside golf course in Portland, Maine.
Riverside Golf Course Sledding/Tubing Hill

Come prepared – there is no equipment rental here. Check out Gorham Bike and Ski for snowshoe rentals or cross-country ski rentals. For more even more rental options, check out Eastern Mountain Sports.

two women snowshoeing down a hill at Riverside Golf Course in Portland, Maine.

Crews at Riverside Golf Course groom 8 kilometers of trails for both classic and skate cross-country skiing. Put on snow shoes and stomp around while you create your own trail through the golf course. After that, fill your need for speed on the sled ridding hills or perfect your triple lutz at the ice rink. Riverside Golf Course is a great way to enjoy Portland, Maine in winter!


Oat Nuts Park

Where: 189 Summit St. Portland, Maine 04103

Website: www.trails.org

Although Oat Nuts breakfast cereal no longer exists, the result of an old marketing ploy to sell more boxes of it lives on as a wooded park within the boundaries of Portland. In 1902, Boston-based Liberty Pure Food Co. offered 50 ft. by 20 ft. parcels of land to customers in exchange for 5 cereal box tops and $2 to handle the legal transfer of the lots. Quite the gimmick, indeed.

Today, a series of rather easy wooded trails pass through this old subdivision of lots which joins and borders the more impressive Presumpscot River Preserve. The trails, especially those within the preserve fronting the Presumpscot River, will have you questioning whether or not you are still within city boundaries. You are.


Deering Oaks Park

Where: Park Ave. & Deering Ave. Portland, Maine 04101

Website: For more info, click here

Designed by the Olmsted Brothers, planners of famous parks throughout the country, Deering Oaks is a peaceful place to relax or take a stroll during your visit. Seasonal activities, such as ice skating on the pond and a summertime splash pool for the kids, keep Deering Oaks a focal point for city dwellers year-round.

arched stone bridge in Deering Oaks Park in Portland, Maine

Storm the historic “castle” at Deering Oaks Park; this building once served as a warming hut for ice skaters braving Portland, Maine in winter. Now, the castle operates as Tiqa bakery and cafe. Plenty of events and festivals take place at Deering Oaks Park during the year; click here for a scedule.


Pack a Picnic

Heading to the islands, lakes or mountains? Bring a picnic, but only if you can find some of the best groceries around town.


Pat’s Meat Market

Where: 484 Stevens Ave. Portland, Maine 04103

Hours: 

  • Mon. – Fri. 6:00 am – 6:00 pm
  • Sat. 6:00 am – 4:30 pm
  • Closed Sun. 

Telephone: (207) 772 3961

Website: www.patsmeatmart.com

Forget about the deli and butcher counter at the grocery store – Pat’s Meat Market has been doing it better since 1917. Everything you need for a picnic, including proper bread for sandwiches, can be found in this old-fashioned neighborhood grocery store.

Pat's Meat Market in Portland, Maine.
Photo Courtesy of Pat’s Meat Market

The deli counter at Pat’s Meat Market has all the cheeses and lunch meats you’ll need to pack the perfect picnic. This neighborhood shop is equal parts butcher, deli and green grocers, even featuring basic pantry staples, local baked goods and a small wine section – everything you want!

Fresh vegetables at Pat's Meat Market in Portland, Maine.
Photo Courtesy of Pat’s Meat Market

A cookout instead of a picnic? Pat’s Meat Market has the best butchers in Portland, Maine and a great selection of steaks, ground beef, sausages, lamb and chicken. From shanks and shoulders to brisket and bacon, Pat’s has the cut you need and the friendly butchers here are ready to help.

The lamb burgers at Pat’s come with a definite Drifters Recommendation! By the way, pick up some burger buns from Mainly Grains while you’re here – they are the best you’ll ever have.


Rosemont Market

Where: 4 locations in Portland and 2 outside the city – see website below for individual locations, telephone numbers and hours.

Website: www.rosemontmarket.com

With 6 locations, it’s easy to find a Rosemont Market near you before heading out for that picnic. Here, stock up on local meats and cheeses, produce, breads and other assorted baked goods. Rosemont Market even has that perfect bottle of wine waiting to go in your picnic basket.

Logo sticker for Rosemont Produce Company in Portland, Maine.

Rosemont Market has been reminding Portland of the importance of real food since 2005. Since then, locals have been shopping here for thoughtfully sourced groceries in a genuine neighborhood environment.


Micucci Grocery

Where: 45 India St. Portland, Maine 04101

Hours: 

  • Mon. – Fri. 8:00 am – 5:30 pm
  • Sat. 8:00 am – 5:00 pm
  • Closed Sun.

Telephone: (207) 775 1854

Website: www.micuccigrocery.com

Micucci Grocery stocks the shelves with Italian imported foods at reasonable prices. The deli counter here is loaded with some of the best cheeses and deli meats on the downtown peninsula; try the Cacio de Roma and Bel Paese – the finest Italian cheeses you will find around.

Micucci Grocery has an extensive wine selection, fresh pastas and sauces, olives, oils and delicious local breads for those picnic sandwiches. Get here early on weekends.


Entertainment

Seeing the sights during your visit to Portland can be hard work; what to do for fun? Find out what the locals do and where they go.


Portland Sea Dogs

Where: Hadlock Field, 271 Park Ave. Portland, Maine 04101

Season: April – September

Websitewww.milb.com/portland

Portland, Maine in winter is rough, so the city rejoices when the Sea Dogs, a Double-A affiliate of the Boston Red Sox, finally take to the field in April. If your visit to Portland jives with baseball season, join the fans who flock here and have a blast heckling the visiting team. Marvel at the rather diabolical-looking mascot Slugger as he helps fans cheer on the Sea Dogs during the game!

Motionhero, Hadlock Field and Slugger, CC BY-SA 3.0

There is limited Portland Sea Dogs parking near Hadlock Field during games and competition for on-street parking is fierce. Instead, walk to the game from town; Hadlock filed is located just off the downtown peninsula.

There are plenty of eating and drinking options near Hadlock Field if stadium fare prices leave you aghast, and they will. Check their official schedule online for game times, promotions and giveaways.


Thompson’s Point

Where: 10 Thompson’s Point Rd. Portland, Maine 04102

Telephone: (207) 747 5288

Website: www.thompsonspointmaine.com

Thompson’s Point is an innovative and hip year round venue incorporating a variety of revolving events and on-site staples. In Winter, get your skates on (or rent theirs) and visit their ice rink. You can even thaw out in a heated yurt with a craft beer! Catch a Summer concert and graze at any of the multiple local food trucks ready to feed your cravings. Visit one of Time Magazine’s “Ten Weirdest Museums in the World” (2014) – The International Cryptozoology Museum, where you may catch a glimpse of Bigfoot.

Sam Van Aken courtesy Ronald Feldman Fine Art, Tree of 40 Fruit – nursery – DSC 0302, CC BY-SA 4.0

If unique horticulture is more your thing not only can you attend the Maine Flower Show here, but on the grounds of Thompson’s Point you will find an installation like no other. 40 Fruit Plaza is the location of a grove of fruit trees by Sam Van Aken who has perfected the art of grafting trees. The Tree of 40 Fruit is just that, one tree that produces 40 different kinds of stone fruits. Optimal times to see the Franken-Fruit-Trees are during Spring flowering and late Summer fruit bearing.

Thompson’s Point also hosts vintage bazaars, craft shows and a place to paint your own pottery that is BYOB (bring your own beer)! Choose between a winery, distillery or brewery for a relaxing drink during your visit. You can even stage your own special event – looking for a classy and classic wedding reception location? For the full spectrum of offerings and details on the finer points, check out www.thompsonspointmaine.com.


Bayside Bowl

Where: 58 Adler St. Portland, Maine 04101

Hours: 

  • Mon. – Thur. 4 pm – 11 pm
  • Fri. 12 pm – 12 am
  • Sat. 11 am – 12 am
  • Sun. 11 am – 11 pm

Telephone: (207) 791 2625

Website: www.baysidebowl.com

Bayside Bowl in Portland, Maine is so much more than just a place to knock down pins – this is an entertainment mecca! Local and national music acts play here on Friday and Saturday and many of the shows are free! For a schedule of upcoming events, click here. Bayside Bowl also has a full service bar and restaurant among the lanes featuring sides, salads, sandwiches and pizzas – check out the menu here.

Bayside Bowl in Portland, Maine.
Photo Courtesy of Tom Couture www.tomcoutureweddings.com

Visit The Rooftoop at Bayside Bowl, where a converted vintage Airstream trailer serving tacos takes pride of place at this open-air venue. There’s even a bar up here along with great views of downtown Portland and the Back Cove. Enjoy free movies on The Rooftop at Bayside Bowl during sundown each Wednesday in summer.

The Rooftop at Bayside Bowl in Portland, Maine.
Photo Courtesy of Tom Couture www.tomcoutureweddings.com

What about the bowling lanes? Bayside Bowl features 20 USBC sanctioned ten-pin lanes, available by the hour. Check here for rates. Visit Bayside Bowl to strike up a good time while being surrounded by live entertainment, food and drink, movies and great sunset views from The Rooftop. You may not bowl a perfect 300 game but you’ll have a perfect time trying. Bowling in Portland, Maine has never been better.

The bowling lanes at Bayside Bowl in Portland, Maine.
Photo Courtesy of Tom Couture www.tomcoutureweddings.com

To keep the fun going, locals book events at Bayside Bowl ranging from birthdays to weddings. This is certainly a lively place within Portland to hang out and have a good time. The PBA (Professional Bowlers Association) has even taken note of the great atmosphere at Bayside Bowl, choosing these lanes to host their Elias Cup Finals in 2017 and the PBA Playoffs in 2019.


Drive-In Theatres

Prides Corner

Where: 651 Bridgton Rd. Westbrook, Maine (6.7 miles via US-302 West from downtown Portland)

When: Memorial Day – September.

Telephone: (207) 797 3154

Website: For details check their Facebook page

Saco Drive-In

Where: 969 Portland Rd. Saco, Maine (13 miles via I-295 South from downtown Portland)

When: Memorial Day – September. 

Telephone: (207) 286 3200

Website: www.thesacodrivein.com

Although Portland’s 2 nearest drive-in theatres are not technically in Portland, they are certainly not far away. Pack a picnic (See our “Pack a Picnic” category above), or stock up on snacks at the concession stand for a night of nostalgia and fun for all the family.


Free Outdoor Summer Films

Where & When: Multiple venues and showtimes, see links below.

Winters here are tough –  that is why locals love watching FREE movies in the park in Portland during the summer! In fact, there are multiple venues throughout the area showing free films outdoors during the warm months.

Congress Square Park in downtown Portland shows all sorts of summer films at dusk on Sundays from June through August, weather permitting. Click on their website www.portlandsummerfilms.com to learn more.

Castrum avisani, Festival de cinema de plein air de visan, CC BY-SA 3.0

In addition to summer films at Congress Square Park you’ll find venues and showtimes throughout the area featuring free outdoor movies in Portland during the glorious summer months. For information on FREE rooftop films at Baysie Bowl (above), click here or check out www.mainetoday.com to find where and when your favorite outdoor summer movies will be screening.


Art, Street Art and A Bit of History

From museums, galleries, murals and even an Eastern Bloc relic, Portland is full of interesting works both new and old.


Portland Museum of Art

Where: 7 Congress Square, Portland, Maine 04101

Hours: See website below for current hours

Telephone: (207) 775 6148

Website: www.portlandmuseum.org

Explore the Portland Museum of Art collection or check out the current visiting exhibit. Don’t miss the “McLellan House” and it’s collection. It is accessed from the museum through a rear annex.

Rennboot, Portland Museum of Arts, CC BY 3.0

Pay $15 admission per adult OR, if time is on your side, visit on Friday evening. The Portland Museum of Art offers “Free on Friday Evenings” from 4:00 pm – 8:00 pm. Do you want to know what is wonderful about this? It is free for everyone, not just residents as is often the case with museums.

The Portland Museum of Art is also home to a cinema dedicated to art house films. For screenings and more information, click here.


First Friday Art Walk

Where: Portland Arts District, Upper Congress St.

When: The first Friday of every month, no matter the weather. 5:00 pm – 8:00 pm

Website: www.creativeportland.com

Added Bonus: METRO, Portland’s Bus Service, is FREE ON ALL ROUTES FROM 4:00 pm – ONLY DURING FIRST FRIDAY ART WALK!

Art galleries, artists studios, and the artistic enterprises in downtown Portland open their doors to the public for a free meet and greet with the local creative community during First Friday Art Walk in Portland, Maine.

Chat with the artists (sometimes over a complimentary glass of wine) and find out if Portland is their muse. First Friday Art Walk in Portland, Maine is a local favourite!


Street Art

Where: Throughout Portland. Take a walk during your visit and find out where!

orange poppy mural on the side of a brick building in Portland, Maine.

Like most urban centres these days, Portland has its own home-grown talent of street artists/graffiti artists. Throughout the city you will find murals reflecting everything from life on the waterfront to abstract oddities.

2 faces spray painted on electrical boxes with the sea in the background on East End Beach in Portland, Maine.

Since 2001 “the graffiti wall” has been one of the rare legal sites in town to showcase local talent. This 100 ft wall on the Eastern Promenade, near the Portland Wastewater Treatment Plant, continues to display scrawled amateur tags alongside larger, exceptional pieces.

Graffiti wall  featuring the Incredible Hulk in Portland, Maine.
Graffiti Wall, Eastern Promenade
Graffiti wall in Portland, Maine.
Graffiti Wall, Eastern Promenade

As is typical of graffiti there are no permanent residencies here. As a result, the life span of each work is dictated by the next artist’s need for a fresh “canvas”!


A Bit of History – The Berlin Wall

Where: 1 Long Wharf, Portland, Maine 04101

No matter how desperately you try to strike off from the tourist path, you will find yourself strolling along Commercial Street on the waterfront during you visit – we guarantee it.

2 sections of the berlin wall with old graffiti.
Paul VanDerWerf from Brunswick, Maine, USA, Berlin Wall Segments (7957482486), CC BY 2.0

It is here on Long Wharf, near the iconic “DiMillo’s” floating restaurant, where you will find 3 slabs from the Berlin Wall. Oddly, these rather historical pieces of masonry are often overlooked by tourists and locals alike!


Casco Bay Ferries

Where: 56 Commercial St. Portland, Maine 04101

Telephone: (207) 774 7871

Website: www.cascobaylines.com 

Intriguing Fact:

Winter in Portland, Maine has caused Casco Bay to freeze on occasion. In 1917 five men drove a truck from Great Chebeague Island to Portland and back again across the ice! Read more about this icecapade here.

yellow and white ferry on water at sunrise in Portland, Maine.
Casco bay Ferries, Portland, Maine

An iconic sight of Portland’s waterfront are the “Casco Bay Ferries” which ferry passengers from the mainland out to the islands of Casco Bay. Within the entire bay the islands are collectively known as “the Calendar Islands” as a result of a historical observation implying it would be possible to visit a different island every day of the year.

In reality this lovely little myth has been debunked and apparently there are significantly less islands, although it seems no-one can agree on exactly how many there are. Who’s counting anyway? One thing you can count on during your Casco Bay cruise is the best view of the Portland skyline from the water.

Casco Bay Ferries not only shuttles islanders and their daily routines from the islands to the mainland and back again, it has also become  a popular day trip unto itself for locals and tourists alike looking for boat tours from Portland, Maine.

There are multiple options for a Casco Bay cruise to choose from however not all are narrated for day trippers on board – some are just island transportation. Check beforehand if a narrated cruise is what you want.

Your Drifter’s Recommendation for a great Casco Bay cruise is the “Bailey Island Run” – one of the best boat rides in Portland, Maine. This is a rather lengthy cruise of just under 6 hours and is seasonal, available only from late June through early September. Pack a picnic and some refreshments (see tips below), allow plenty of time and enjoy a day on the water. Click here for more information.

Insider Tips

  • You can bring beer or wine along for on board consumption during your Casco Bay cruise. We have done this many times ourselves, just be discreet and don’t ruin this for everyone else by getting trashed. Remember this is not a booze cruise, rather this is a nice privilege that can be revoked at any time by the company. Consumption of hard liquor on board is prohibited.
  • Bring extra layers of clothing. It may be the most glorious Summer day on land but it can get quite chilly once you are out on the water.
  • Although the narration is a nice added touch, it can be difficult to decipher; position yourself near the ship’s intercoms.

Seasonal

Even Portland, Maine in winter is full of yearly delicacies loved by locals. Look for these signs of the seasons during your visit.


Tulips at Fessenden Park

Where: Fessenden Park, Oakdale Neighbourhood, Intersection of Brighton Ave. and Deering Ave. Portland, Maine. 04103

When: Mid May.

Embraced by locals as a sure sign of having turned the corner, the colourful tulip beds are a welcome sight after the long, bleakness of Portland, Maine in Winter.

Tulips, Fessenden Park, Oakdale Neighbourhood, Portland, Maine.
Tulips, Fessenden Park, Oakdale Neighbourhood, Portland

pink tulips in a park Tulips, Fessenden Park, Oakdale Neighbourhood, Portland, Maine

This small triangular park is a perennial favourite and a popular photo op for the latest graduates from the University of Southern Maine, whose campus is scattered all around this intersection.


Porchfest Portland

When and Where: For the Porchfest Portland Facebook page, click here. This special event happens but once a year.

Porchfest Portland is a great way to see (and hear) more of the city during your visit. What is it? Porchfest is a music festival held throughout the country in various communities. Held only once a year, Porchfest encourages locals to gather around front porches which act as venues for local musicians. Currently, Porchfest is held in over 2 dozen communities throughout the U.S. and Canada.

If you catch a Porchfest event during your visit to Portland, or any community offering this event, consider yourself lucky indeed. In short, Porchfest takes the notion of a block party and adds an extra twist of entertainment for good measure. The best part: It’s free and everyone is invited!


Old Port Festival:

Where: The festival is held throughout the Old Port with the parade beginning at the top of Exchange St. in the Old Port.

When: The second Sunday of June.

Website: www.portlandmaine.com

This is a festival held to herald the arrival of Summer. The festivities begin with a parade, the highlight of which is “Shoestring Theater” and their gigantic, intricate hand-made puppets

Puppets at the parade for the Old Port Festival in Portland, Maine.
Photo Courtesy of Sarah Beard Buckley
Puppets at the parade for the Old Port Festival in Portland, Maine.
Photo Courtesy of Sarah Beard Buckley

 Typical festival attractions include food stalls, food trucks, arts and crafts, music and vendors from local businesses.


Valentine Bandit 

Perhaps Portland’s most beloved tradition is that of the Valentine Bandit. For over 40 years this mystery individual has been spreading the love throughout the city, often in the most spectacular and unbelievable ways.

Valentine Bandit heart from Portland, Maine.

Working through the night on the eve of Valentine’s Day, this individual completes what can only be described as a superhuman feat. Not only does he/she/they leave a simple heart taped to just about every building downtown and outlying neighbourhoods, he/she/they also drape and cover city landmarks with heart banners.

There are 2 factors making this event even more impressive and intriguing:

  1. This is Portland, Maine in winter – cold is an understatement.
  2. In an age of instant information and the celebrity of revealing an online exposure (not that kind of exposure), the Valentine Bandit has retained their anonymity for over 40 years.

Leaf Peeping in Autumn

When: End of September through the end of October, roughly.

Leaf peeping in New England is certainly no secret – tourists from across the world come to witness the blaze and variety of color in the fields and mountains. Portland is no different and you’ll find plenty of spots in the city to experience the showy spectacle.

red and green autumn leaves in Portland, Maine.

Our favorite place in Portland for leaf peeping is Evergreen Cemetery, featured above in this post. Stroll around the grounds here and feel the heat of the colors, made even more vivid when seen against a clear blue sky! Or pick any residential, leafy street to walk down – each has a bright tree to guide you.


Need More Info?

Fancy a more in depth view of where to go leaf peeping in New England? Click on the book below to find the best road trips New England has to offer for taking in her colourful Autumn foliage. Lonely Planet has been one of the top go-to guides for travellers for more than 40 years!

New England Fall foliage Road Trips Lonely Planet book.


Christmas Lights

Any town can string a few lights around a tree or telephone pole at Christmas and call it good. Portland, Maine in winter is simply like no other place when it comes to decorating their trees with Christmas lights and you will soon notice this.

christmas light at tommys park in Portland, maine.

christmas light at longfellow square in portland, maine.

Portland, Maine in winter sees public squares, parks, buildings, trees and even statues display rather thoughtful arrangements of twinkling lights. You will even notice a Dr. Suess-esque theme, evident in the trees around Longfellow Square at the intersection of State St. and Congress St.


One Last Thing…

Congratulations if you have read thus far. We know this post is a behemoth and we have barely scratched the surface of Portland’s delectable delights. There are so many more local’s favourites but we have to call time on this one – on ourselves! However if any of our Portland friends are reading this we would love to hear your input in our comments section below. Please share all of the places we never got around to mentioning!

To visitors, we hope you enjoy Portland like a local – as a tourist!


We’d like to extend a special thank you to all of the businesses and individuals who contributed photos for this post.

We are affiliates with Lonely PlanetTherefore if you purchase a Lonely Planet travel guide after clicking on one of the text links or books within this post we receive a nominal commission from them, at no extra cost to you.


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28 Comments

  1. Great post! As a local, you have hit pretty much everything! One update to make – the Great Lost Bear doesn’t give you a beer for the trivia question. They stopped doing it a while ago as it turns out it’s illegal to give away free alcohol. 🙂

    • Marit,

      That’s too bad, however I believe there is a simply way around this pesky law that says you cannot give away free alcohol: The Great Lost Bear pays for each pint that somebody wins! That way, they are not giving away free beer – they’re more or less buying it for the trivia question winners. That would work, yeah?

      Thanks for the update!

      Your Drifters,
      Jerry and Fiona

  2. You’ve got a little something for everyone is this guide! I had always thought of Portland, Oregon and not Maine – but now I see that there’s a ton of things to do. I feel like this would also be such a great trip over the summer, the parks, the hills the quirky shops around town. Thanks for a virtual tour of Portland, would love to visit someday.

  3. I’m heading to Portland, Maine this May! I can’t wait to explore it. Thanks for this extensive post. These tips will be super helpful for my trip. The fish and chips and whoopie pies are calling my name!

  4. WOW! Been to Portland many times, yet you have opened my eyes wide! I mean, I always loved Portland, but now know how much I was missing in my quick 24 hours here and there. I just have to eat at the Bayou Kitchen. And now am fully fascinated with the Mackworth Island State Park and its history. And Porch Fest? LOVE it.

    • Michael,

      We love to hear the enthusiasm you have for Portland! Will you make it back anytime soon? If so, we are happy to have shared a few great places for you to explore.

      Your Drifters,
      Jerry and Fiona

  5. This is such a complete and thorough guide, and I’ve always wanted to go back to Maine since we went to Acadia National Park as a kid! This looks like the perfect kind of town to check out a farmers market, and I love finding stores like Strange Maine, so I’d be sure not to miss that!

  6. I have never been to Portland Maine and it looks like a great place to travel to for a long weekend getaway. That sign at The Bayou Kitchen is so fun and I like establishments that are located in old buildings. I’m also a huge Cajun fan so this is definitely a place I would stop by. Love how you gave detailed information about transportation. That really helps out a ton!

    • Candy,

      Portland has become a food destination, no doubt. In fact, the city is 2nd or 3rd per-capita to San Francisco for the number of restaurants to people. So much more than just lobster, although they are good too.

      Your Drifters,
      Jerry and Fiona

  7. I love Portland during my short time here (I even went on honeymoon here back in 2010 during a road trip of New England). What I loved the most was the lobsters…totally lush and melted in my mouth. Love the locals here, very friendly. I remember that more than exploring the town! 😀

    • Danik,

      There is a famous marathon called Beach to Beacon you would love! There may even be a lobster waiting for you at the finish line! Happy you had such a great time there.

      Your Drifters,
      Jerry and Fiona

  8. We’ve never been to Portland, but would love to visit someday. We usually prefer to go to less touristy places when we travel, and discover spots where locals go to, so this post is perfect! We will certainly head to the local market, but also visit the Evergreen Cemetery, since it looks like there are several beautiful funerary monuments and sculptures!

  9. I always find local guides like this very comprehensive with lots of local favourites included and recommended 🙂 Sounds like there are plenty of things to do and eat around the city. Plus its shopping scene is definitely interesting. I could spend hours at the Strange Maine. The items on display looks very inviting!

  10. What a great round-up of things to do in Portland! The Great Lost Bear sounds like a place I would love. Hope to visit soon and take some of your suggestions!

  11. What a thorough post, enough to entice anyone to go straight to Portland (well, in the spring). I was there once as a child but would love to return. Silly’s and the Vientiane Market ( mmm), outdoor summer movies and free art walks are very appealing to me. Thank you for all the insider’s tips.

  12. Been there and done some of that. Realize there is a lot more to see and do but a return trip seems unlikely. All our trips there were special.

    • Hero,

      Yes, we loved Portland and it is good to hear from folks like you who feel the same. Many good memories there, no doubt. Thanks for sharing your thoughts on Portland, Maine.

      Your Drifters,
      Jerry and Fiona

  13. Awwww you guys! I am sitting here in Portland Oregon and now am missing Portland Maine. I have been to all the places and done all the things you posted about- even worked at a bunch of them! Thank you for the reminder of what a special place it is. We love it here and are very happy but east coast Portland will be in our hearts forever. We miss you and hope you are having a wonderful adventure. Lots of love from the 3 Bs ❤️

    • Kristen!

      Yes, Portland, Maine is a special place indeed and we were so lucky to enjoy it along with yourself, Rock and Marley!

      Our adventure continues – we have put over 30,000 miles on the VW, having been to the Baja Peninsula twice already. We are also doing a lot of house sitting at the moment, meeting great fur-babies and great folks too along the way.

      We miss you guys, too! Thanks for the comment, and take care of each other. Portland ROCKS! – both of them!!

      Your Drifters,
      Jerry and Fiona

  14. Charles Foss

    Great posts on Portland Maine! I loved the back alley feel, where real people go to experience life.

    I will be right at home at Evergreen Cemetery, especially after my expiration date. I love the light and the seasons and the spirits.

    When you return to Portland, The Great Lost Bear will still have many growls left for you two at the end of my tab.

    • Charlie,

      It’s so good to hear from you! Keep a seat for us at the Great Lost Bear! We really do miss Maine and we hope to return soon one day. Portland was such a great place to be for 14 years.

      Thanks for the great comment, and the great offer for us to order all the Schlitz pounders we want! We hope to see you again, Charlie. You are a great friend to us both.

      Your Drifters,
      Jerry and Fiona

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