Last Updated on September 12, 2020
Following the locals is the best way to really see a place, especially during a quick getaway. Keep that in mind when planning a weekend in Portland, Maine and follow our suggestions for getting away form the tourist trail. Sure, enjoy the popular sights and places to visit, then see how easy it is find local favourites. We lived here for 14 years, so take our knowledge of Portland and see more of this coastal Maine city.
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A Unique Weekend in Portland, Maine
We’ll reveal the best local parks, neighbourhood restaurants, gourmet markets perfect for picnic supplies, drive-in theatres, quirky shops and insider tips for year-round fun. From getting outdoors or simply grabbing an afternoon pint, we cover a lot of ground so keep on reading. Whether you plan a weekend escape or just a day trip to Portland, Maine our suggestions give a great local perspective of the city.
Getting to Portland, Maine for the Weekend
We’ll assume you already have your own vehicle for your weekend in Portland, Maine. If not, arriving to and moving on from the city is easy. The airport is only minutes from town and the combination bus/train station is even closer. Regular bus connections from Boston mean your weekend in Maine is certainly within reach, even without your own vehicle. We’ll look at those options and more below.
We even include information on getting around Portland, Maine by public transportation. The city has a great network of buses which bring you around the city and beyond. See Getting Around by Bus at the end of this section.
Flying to Portland, Maine
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 (see below) operates a route to downtown from the Jetport – look for the bus stop directly outside baggage claim. Find more information on the airport route online. More information and links for the METRO are just below.
Speaking of Flying Into Portland…
Car rental at Portland International Jetport is easy; all the major agencies are located just a few steps from the baggage claim area. There’s no need to take a shuttle bus to the rental facility – you can check-in and be on your way in a matter of minutes.
You’ll find the following car rental agencies located just opposite the baggage claim area:
Buses and Trains to Portland, Maine
The Portland Transportation Center handles trains and buses to and from the city to Boston’s South Station. In addition, bus service from Portland Transportation Center includes routes 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.
Getting Around by 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. Get more information regarding METRO fares and schedules online and take the bus during your next visit.
Eating & Drinking in Portland, Maine
The denizens here certainly have their favorite bars and restaurants; follow one during your trip to Portland, Maine and and see where they go. The well-known tourist spots for eating and drinking are great but the neighbourhood establishments are even better! Step away from the downtown peninsula during your visit and check out of some these charming neigbourhoods yourself.
The Bayou Kitchen
Where: 543 Deering Ave. in Portland’s Woodfords Corner Neighborhood.
- 8:00 am – 3:00 pm, Thursday through Saturday and Monday
- 9:00 am – 3:00 pm Sunday
- Closed Tuesday and Wednesday
Telephone: (207) 774-4935
Looking for one of the best breakfasts in Portland, Maine? Step away from downtown and head to the Woodfords Corner neighborhood in search of true flavour. 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 because this place fills up quick. 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 to jazz up your omelette. Keep the heat going with a piece of jalapeño & cheddar cornbread.
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 omelette featuring crawfish tail meat, definitely comes with a strong Drifter’s 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!
Where: 1135 Forest Ave. between Portland’s Woodfords Corner and Deering Junction neighbourhoods.
Hours: 11:00 am – 8:00 pm, daily.
Telephone: (207) 878-3240
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 over 30 years for some of the best fish and chips and hand cut onion rings in town!
The menu goes beyond fish and includes battered and fried calamari, clams, oysters and scallops! Every Monday and Tuesday enjoy Susan’s Fish-n-Chips famous special: two 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.
Don’t miss Susan’s Fish-n-Chips homemade coleslaw – the best you’ll 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. So pack a picnic for that day trip and bring some coleslaw from Susan’s Fish-n-Chips.
The Great Lost Bear
Where: 540 Forest Ave. in Portland’s Oakdale Neighbourhood.
Hours: 11:30 am – 11:30 pm, daily.
Telephone: (207) 772-0300
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, the Great Lost Bear keeps it real with $1.99 Schlitz pounders for traditional brew lovers.
The cozy atmosphere here – neon signs, antique photographs, vintage beer memorabilia and assorted ephemera – certainly makes this one of the best places to go in Portland, Maine to escape the tourists while enjoying a locally-brewed pint.
The Great Lost Bear has a huge menu filled with uniquely named dishes. For example, try not to laugh as you order the Almighty Cheesus Burger or the Mother and Child Reunion (fried chicken and fried egg), served between two grilled cheese sandwiches!
The funny-sounding dishes won’t prepare you for the serious portions served here – consider yourself warned. Order some of the best burgers in town and pair them with a microbrew from the almost world-famous Great Lost Bear Beer Menu.
Where: 157 Noyes St. in Portland’s Oakdale Neighbourhood.
- 10:30 am – 9:00 pm, Monday through Saturday
- Closed Sunday
Telephone: (207) 774-7311 or (207) 879-1614
We lived around the corner from Vientiane Market in Portland’s Oakdale neighborhood. We ate from 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 delicious, 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 food in Portland, Maine – according to the locals, anyway. Enjoy your meal at one of the several tables provided or order it for take-away instead.
NOTE: Vientiane Market uses a star system when taking your order: zero means no spice and five stars is full-spice. Concerned staff will warn you if you opt for anything above three stars!
The Jewel Box
Where: 644 Congress St. in downtown Portland, Maine.
Hours: 5:00 pm – 1:00 am, daily.
Telephone: (207) 747-5384
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.
Once inside it’s evident the raison d’être of this hipster hideaway is the cocktail menu. You can also grab a beer or a glass of wine here too, but this isn’t your typical bar, so don’t expect an extensive beer and wine list.
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 juices creating one-of-a-kind concoctions with equally idiosyncratic names. There’s also a small tapas menu at the Jewel Box if your’re feeling a bit peckish.
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 arriving 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.
Bubba’s Sulky Lounge
Where: 92 Portland St. between Portland’s Bayside and Parkside neighbourhoods.
- 8:00 am – 7:00 pm, Sunday through Thursday
- 8:00 am – 1:00 am, Friday and Saturday
- 80’s Night every Friday from 8:30 pm – 1:00 am
- The Everything Dance Party every Saturday from 9:00 pm – 1:00 am
Telephone: (207) 828-0549
Note: Bubba’s Sulky Lounge is cash only!
Your unique weekend in Portland, Maine isn’t complete without an afternoon beer at Bubba’s Sulky Lounge! Words do no justice describing this cherished local 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 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! Bar chairs aren’t the only thing swiveling at Bubba’s; your head will swivel as you marvel at the hundreds of vintage metal lunch boxes 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.
Where: 606 Congress St. in downtown Portland, Maine.
Hours: 5:00 pm – 1:00 am, daily.
Happy Hour: 5:00 pm – 7:00 pm, daily.
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. A blackboard above the booths highlights the day’s menu. Oft described as Portland’s quintessential dive bar, the DTL as it’s 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. This spot is absolutely perfect for a 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 (see below).
Downtown Lounge is also renowned locally 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 three or four narrow steps to climb to make it to the loo, this is the ultimate intoxication indicator!
Two Fat Cats Bakery
Where: 195 Lancaster St. in Portland’s hip and trendy Bayside Neighbourhood.
- 8:00 am – 3:00 pm, Tuesday through Saturday
- Closed Sunday and Monday
Telephone: (207) 347-5144
Looking for scratch-made cakes and pies during your Portland, Maine getaway? It’s good to succumb to your sweet tooth and Two Fat Cats Bakery is the place to indulge those cravings. This is now your chance to try the official Maine state treat – the whoopie pie. Two Fat Cats is the place for the best homemade cakes and pies in the city so check them out during your next getaway.
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 need a cake for a special occasion our 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 scarf-down a few slices in one sitting!
Standard Baking Co.
Where: 75 Commercial St. in Portland’s Old Port.
- 7:00 am – 6:00 pm, Monday through Friday
- 7:00 am – 5:00 pm, Saturday and Sunday
Telephone: (207) 773-2112
Alright, so this is definitely not a hidden gem but it is still a gem. In Summer, queues form out the door during the morning. In Winter, locals reclaim this sweet little bakery for themselves without having to jostle with the out-of-towners.
What’s good here? Everything, but we’ll highlight our favourite bread at Standard Baking Co. – the stirato loaf. Whether you’re going on a picnic or perhaps just fancy some of the best crusty bread around, pick up the stirato and taste it for yourself. Crusty on the outside and slightly chewy on the inside, this is as close to perfection as you’ll get. Standard Baking Co. have mastered the art of real bread making stateside.
Unique Shopping in Portland, Maine
Go home with a truly unique reminder of your trip to Portland, Maine or just have fun browsing with the locals. The following suggestions certainly aren’t souvenir shops for tourists. We’ve included very local-orientated shops providing a genuine feel for the city and her inhabitants.
Where: 578 Congress St. in downtown Portland, Maine.
- 11:00 am – 7:00 pm, daily.
Phone: (207) 771-9997
What’s in a name? Everything, in this case! If you’re looking for quirky, bizarre, random, kitsch – and that’s just the decor of this tiny little local curio, then look no further than the aptly-named Strange Maine. Every inch and corner of this downtown shop is full of stuff to keep you engaged.
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 simply 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 bizarre boutique – we guaranteed something here will make you smile! Although Strange Maine is normal turf for local collectors and aficionados of vintage music and pastimes, you’ll likely walk away with a Pet Rock or a Stretch Armstrong toy accompanying you. Come here and make your trip to Portland, Maine a pleasantly strange one!
Where: 500 Congress St. in downtown Portland, Maine.
- 10:00 am – 6:00 pm, Monday through Saturday
- 11:00 am – 5:00 pm, Sunday
Telephone: (207) 774-1241
Website: Visit Material Objects on Facebook.
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 during your visit.
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 the cold at bay, Material Objects is your only go-to.
Hidden among the racks you may find that one-of-a-kind kit that’s been eluding you at the other clothes shops in town. 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. in Portland’s Bayside Neighbourhood.
Hours: See website below for current hours.
Phone: (207) 780-0634
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. foot 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 your weekend in Portland, Maine.
Fortunately, this city has a great stock of old homes. Unfortunately, people update (ruin) the soul of these homes. Fortunately, Portland Architectural Salvage insists these old souls live on by providing these cast-off wares to renovators and collectors who agree.
Those forgotten fixtures exist here and blend in 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 town!
Portland, Maine Getaways in the Great Outdoors
Craving some fresh air and a bit of exercise? Your’re never far from urban and wooded hiking trails, all within city limits. Don’t miss an opportunity to keep active when you visit Portland, Maine during any season. Get out there and see for yourself!
Where: 672 Stevens Ave. in Portland’s Deering Neighbourhood.
- 8:00 am – 4:30 pm, daily
Phone: (207) 808-5452
A National Historic Landmark, Evergreen Cemetery 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. Are you visiting Portland, Maine during winter? Evergreen Cemetery is a great place to snowshoe and cross-country ski. This is also a great place to come for autumn leaf peeping in a sombre, yet oddly appealing location.
In short, Evergreen Cemetery is one of the best places in Portland, Maine to enjoy spring and autumn foliage. Staying in town but you don’t have a car? Take the Metro from the Pulse station downtown! Routes 9A and 9B drop you directly in front of Evergreen Cemetery.
Standpipe Park or Sumner Park or Top of the World Park
Where: North St. between Quebec and Melbourne Streets in Portland’s Munjoy Hill Neighbourhood.
Looking for the best views of Portland, Maine? 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 Park. Names aside, locals agree this is the best view of the city!
A simple path leads through this acre-sized park to four wooden benches overlooking downtown, the Back Cove and beyond. Come here for that ultimate Portland selfie, then take a seat to ponder perhaps another weekend trip to Maine soon!
Biking & Hiking Trails in Portland, Maine
Discover great hiking in Portland, Maine on over 70 miles of wooded and urban trails. These paths 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, so get out and stretch those legs during your stay!
Looking for bike trails in Portland, Maine? There are plenty of mixed-use paths throughout the city to choose from. If you left your bike at home visit enCYCLEpedia or Gorham Bike and Ski for the best rentals in town.
Check out the Portland Trails interactive map online or opt for a classic map. Visit the website above to learn more about this nonprofit urban land trust. Get out and enjoy miles of hiking in Portland, Maine and some of the best paved bike trails in the entire state!
Mackworth Island State Park
Where: Andrews Ave. Falmouth, Maine. Take US Route 1 north from Portland and follow signs for Mackworth Island – the island is connected to the mainland by a causeway.
Admission: Adult Maine resident: $3. Adult non-resident: $4. Senior non-resident: $1.
This 100-acre wooded island has a rather dark history surrounding the Governor Baxter School For The Deaf. Today 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.
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 just off the trail, as is a small pine grove where you’ll find the fairy village of Mackworth Island. Above all, don’t leave the island without constructing your own fairy house for these tiny forest dwellers – it’s bad luck if you don’t!
Oat Nuts Park
Where: 189 Summit St. Portland, Maine
Although Oat Nuts Breakfast Cereal no longer exists, the result of an odd 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! Come here for the ultimate escape from the city during your stay.
Deering Oaks Park
Where: Park and Deering Avenues in Portland’s aptly named Parkside Neighbourhood.
Website: For more info visit www.portlandmaine.gov
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 you Portland, Maine weekend break. Seasonal activities such as ice skating on the pond, a farmers market (see Farmers Markets below) and a summertime splash pool for the kids make Deering Oaks a focal point for locals year-round.
Storm the historic castle at Deering Oaks Park; this building once served as a warming hut for ice skaters. Plenty of events and festivals also take place at Deering Oaks Park throughout the entire year.
Pack a Picnic
Heading to the islands, lakes or mountains during your visit? Bring a picnic, but only with some of the best gourmet foods around. If your weekend in Portland, Maine includes self-catering then you must check out some of the locally owned grocery stores in town.
Pat’s Meat Market
Where: 484 Stevens Ave. in Portland’s Deering Center Neighbourhood.
- 6:00 am – 6:00 pm, Monday through Friday
- 6:00 am – 4:30 pm, Saturday
- Closed Sunday
Telephone: (207) 772-3961
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, is found in this old-fashioned neighborhood grocery store.
The deli counter at Pat’s Meat Market has the cheeses and lunch meats you’ll need for perfect picnic. This neighborhood shop is equal parts butcher, deli and green grocers and even features local baked goods and a small wine section – everything you’ll ever need for that picnic!
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 their friendly butchers are ready to help.
The lamb burgers at Pat’s come with a definite Drifter’s Recommendation! By the way, pick up some burger buns from Mainly Grains while you’re here – they are the best you’ll ever have and we know you’ll agree!
Where: Four locations in Portland and two outside the city – see website below for individual locations and hours.
With 6 locations it’s easy to find a Rosemont Market near you before heading out for that picnic. 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.
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.
Where: 45 India St. in Portland’s Old Port.
- 8:00 am – 5:30 pm, Monday through Friday
- 8:00 am – 5:00 pm, Saturday
- Closed Sunday
Telephone: (207) 775-1854
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, sauces, olives and delicious local breads for those picnic sandwiches. Get here early on the weekends to beat the crowds, especially during summer months.
When & Where:
- End of April through November: Saturday, 7:00 am – 1:00 pm at Deering Oaks Park (see above).
- May through November: Wednesday, 7:00 am – 1:00 pm at Monument Square in Downtown Portland
- December through mid-April: Saturday, 9:00 am – 1:00 pm at 631 Stephens Ave. in Portland’s Deering Neighbourhood.
- We’ve included a map of these locations for your convenience.
Everyone loves farmers markets and locals here get to enjoy them throughout the year! Even the long Maine winters can’t stop the market activity and folks couldn’t be happier. The venues change throughout the year so plan accordingly.
During winter months the market (mercifully) moves to an indoor location in the Deering neighbourhood. For 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 Portland, 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!
Things to Do During Your Weekend Trip to Portland, Maine
This article is all about tourist sights and normal places many locals enjoy. The best Portland, Maine getaways feature the perfect balance of the two. Below are some lesser-known attractions most visitors either skip or are completely unaware of.
See a Portland Sea Dogs Baseball Game
Where: Hadlock Field, 271 Park Ave. in Portland’s Parkside Neighborhood.
Season: April through September
Winters here are rough, so the city rejoices when the Sea Dogs, a Double-A affiliate of the Boston Red Sox, begin the season in April. If your visit to Portland jives with baseball season, join the fans 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!
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 Field is located just off the downtown peninsula. There are plenty of eating and drinking options near Hadlock Field if stadium food prices leave you aghast, and they will. Check their official schedule online for game times, promotions and giveaways.
Where: 10 Thompson’s Point Rd. Portland, Maine
Telephone: (207) 747-5288
Thompson’s Point is an innovative and hip year round venue incorporating a variety of revolving events and on-site staples. Get your skates on in winter (or rent theirs) for a visit to their ice rink. You can even thaw out in a heated yurt with a craft beer!
Catch a summer concert and graze at 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’ll likely catch a glimpse of Bigfoot and other strange phenomena.
If unique horticulture is your thing then check out the annual Maine Flower Show held here. Thompson’s Point is also home to a horticultural installation like no other; 40 Fruit Plaza contains a grove of fruit trees by Sam Van Aken, a master at the art of grafting. The Tree of 40 Fruit is just that, one tree producing 40 varieties 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 (PYOP) that’s also 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 for a classy or classic wedding reception. For the full spectrum of offerings check out www.thompsonspointmaine.com.
Where: 58 Adler St. in Portland’s Bayside Neighborhood.
- 4:00 pm – 11:00 pm, Monday through Thursday
- 12:00 pm – 12:00 am, Friday
- 11:0000 am – 12:00 am, Saturday
- 11:00 am – 11:00 pm, Sunday
Telephone: (207) 791-2625
Bayside Bowl in Portland, Maine is 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! Bayside Bowl has a full service bar and restaurant among the lanes featuring sides, salads, sandwiches and pizzas – check out their menu.
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.
What about the bowling lanes? Bayside Bowl features 20 USBC sanctioned ten-pin lanes, available by the hour. Check online for open bowling rates. Visit Bayside Bowl to strike up a good time and enjoy live entertainment, food, drink, movies and great sunset views from The Rooftop.
You won’t bowl a perfect 300 game but you’ll have fun trying. Bowling in Portland, Maine has never been better than this. To keep the fun going, locals book events at Bayside Bowl ranging from birthday parties to weddings.
Prides Corner Drive-In Theater
Where: 651 Bridgton Rd. Westbrook, Maine, approximately 6.7 miles via US-302 West from downtown Portland.
When: Memorial Day through September
Telephone: (207) 797-3154
Website: For details check out their Facebook page
Saco Drive-In Theater
Where: 969 Portland Rd. Saco, Maine, approximately 13 miles via I-295 South from downtown Portland
When: Memorial Day through September
Telephone: (207) 286-3200
Although the two nearest drive-in theaters aren’t technically in the city, they are nearby. Pack a picnic (see above), or stock up on snacks at the concession stand for a night of nostalgia and fun while enjoying your weekend in Portland, Maine.
Free Outdoor Summer Films
Where & When: Multiple venues and showtimes – see links below for more details.
Summers here are short and that’s why locals love watching FREE outdoor movies! In fact, there are multiple venues here showing free films outdoors during warmer months. Congress Square Park in downtown Portland shows all sorts of summer films at dusk on Sunday from June through August, weather permitting. Click on their website at www.portlandsummerfilms.com to learn more.
In addition to summer films at Congress Square Park you’ll find venues and showtimes throughout the area featuring more free outdoor movies during the glorious summer months. For information on FREE rooftop films at Bayside Bowl (above) check their movie schedule or check out www.mainetoday.com to find where and when your favorite outdoor summer movies are screening.
Art, Street Art and A Bit of History
From museums, galleries, murals and even an old Eastern Bloc relic, the city is full of interesting works both new and old. So take a stroll down a side street during your visit and be on the lookout for assorted urban art installations throughout Portland, Maine.
Portland Museum of Art
Where: 7 Congress Square in Downtown Portland
Hours: See website below for current hours
Telephone: (207) 775-6148
Explore the Portland Museum of Art collection or check out the current visiting exhibit. Don’t miss the historic McLellan House and its collection. The McLellen House, a National Historic Landmark, is accessed from the museum through a rear annex.
Pay $15 admission per adult or visit on Friday evening. The Portland Museum of Art offers “Free on Friday Evenings” from 4:00 pm – 8:00 pm. Do you know what’s 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 visit their cinema page.
First Friday Art Walk
Where: Downtown throughout the Portland Arts District, located on Upper Congress St.
When: 5:00 pm – 8:00 pm on the first Friday of each month.
Added Bonus: Portland’s METRO bus service is free on all downtown routes from 4:00 pm only during First Friday Art Walk.
Art galleries, artists studios and other artistic enterprises in Downtown Portland open their doors for a free meet and greet during the First Friday Art Walk. Chat with the artists, sometimes over a complimentary glass of wine, and find out if Portland is their muse.
Local Street Art
Where: Throughout the city! Simply take a walk around during your trip to Portland, Maine and be on the lookout for plenty of urban art. Like most urban centres these days, Portland has its own home-grown talent of street/graffiti artists. Throughout the city are murals reflecting everything from life on the waterfront to other assorted abstract oddities.
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 displays scrawled amateur tags alongside larger, exceptional pieces. Typical of graffiti, there are no permanent residencies on the wall here. As a result, the life span of each work is dictated by the next artists need for a fresh “canvas”!
A Bit of History – The Berlin Wall in Portland, Maine
Where: Long Wharf in Portland’s Old Port.
No matter how desperately you try to stray from the tourist path, you will find yourself strolling along Commercial Street on the waterfront during you visit – we guarantee it. This is a tourist draw and a true working waterfront, as real and local as you’ll find anywhere in the city.
On Long Wharf near the iconic DiMillo’s Floating Restaurant are three concrete slabs from the Berlin Wall. Oddly, these rather historical pieces of masonry are often overlooked by locals and visitors enjoying a weekend in Portland, Maine.
Casco Bay Ferries
Where: 56 Commercial St. in Portland’s Old Port.
Telephone: (207) 774-7871
An iconic sight of Portland’s waterfront are the Casco Bay ferries which shuttle passengers from the mainland to nearby islands. One of the best ways to enjoy a weekend in Portland, Maine is to hop on one of those ferries. There are multiple options for a Casco Bay cruise to choose from. Some of these are narrated, stay-aboard cruises and others offer a chance to explore the islands for a few hours.
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 lengthy cruise of just under six hours and is seasonal from late June through early September. Pack a picnic and refreshments (see tips below), allow plenty of time and enjoy a day on the water.
Within Casco Bay the islands are collectively known as the Calendar Islands as a result of a historical observation implying it’s possible to visit a different one each day of the year. In reality this lovely little myth has been debunked; apparently there are significantly less islands but no-one agrees on exactly how many there are. Who’s counting anyway?
In reality this lovely little myth has been debunked; apparently there are significantly less islands but no-one agrees 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 has frozen in the past. In 1917, five men drove a truck from Great Chebeague Island to Portland and back again across the ice! Read more about this icecapade online. You’re unlikely to encounter that during your weekend in Portland, Maine – we hope!
- You can bring beer or wine for consumption on board during your Casco Bay cruise. We’ve done this many times, however be discreet and don’t ruin this for others by getting trashed. Remember, this isn’t a booze cruise – this nice privilege can be revoked at any time by the company. Consumption of hard liquor on board is prohibited.
- Bring extra layers of clothing. Even the most glorious summer day on land means a chilly breeze on the waters of Casco Bay.
- Although the narration is a nice added touch, it can be difficult to decipher; position yourself near the ship’s intercoms in this case.
Seasonal Portland, Maine Getaway Ideas
Winters here are cold and snowy but that doesn’t mean your Portland, Maine weekend getaway will be cancelled. Discover where locals go to sled, snowshoe and cross-country ski in the city. In fact, every season has something to offer visitors and we know you’ll agree.
Tulips at Fessenden Park
Where: Fessenden Park, located at the intersections Brighton and Deering Avenues in the Oakdale Neighborhood
Embraced by locals as a sure sign of having turned a seasonal corner, these colourful tulip beds are a welcome sight after a long winter. This unassuming spot simply comes alive during May so make it to this park during that time if you can.
This small triangular space is a perennial favourite and a popular photo op for the latest graduates from the University of Southern Maine, whose campus is scattered around this park in Portland’s Oakdale Neighbourhood.
Winter Activities at Riverside Golf Course
Where: 1158 Riverside St. Portland, Maine
Hours: 24 hours a day/7 days a week during winter months only.
Do you plan to visit Portland, Maine in winter? If so, celebrate all things cold and snowy at Riverside Golf Course during your stay! This municipal golf course becomes an all-purpose winter playground open to everyone as soon as the snow flies. The entire course is open 24/7, providing free access to sledding hills, cross-country skiing trails, snowshoeing paths, an ice skating rink and acres of fat tire biking trails!
Come prepared – there is no equipment rental here. Check out Gorham Bike and Ski for snowshoe rentals or cross-country ski rentals. For even more rental options, check out Eastern Mountain Sports and get ready to have some fun during your visit!
City crews groom 8 km of trails for both classic and skate cross-country skiing. Put on your snow shoes while stomping around and create your own trail through the golf course. After that, fill your need for speed on the sled riding hills or perfect your triple lutz at the ice rink.
When and Where: For information check out the Porchfest Portland Facebook page. 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 which takes place 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 two dozen communities throughout the U.S. and Canada.
Consider yourself lucky indeed to catch this local event during a weekend getaway in Portland, Maine. Porchfest takes the notion of a block party and adds an extra twist of entertainment for good measure. It’s totally free and everyone is invited!
Search For the Valentine Bandit
When: Valentine’s Day
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.
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 the bandit leave a simple heart taped to buildings throughout the city, they also drape and cover Portland landmarks with heart banners.
Two factors make this once-a-year event even more impressive and intriguing:
- This is Portland, Maine in winter – cold is an understatement and the Valentine Bandit never misses a beat.
- In an age of instant information and the celebrity of online exposure (not that kind of exposure!), the Valentine Bandit has retained their anonymity for over 40 years.
Congratulations for making it this far! This article is a behemoth and we’ve barely scratched the surface of delectable delights of lesser-known attractions in Portland Maine for a weekend getaway. There are so many more local favourites to seek out for yourself.
We’d like to extend a special thank you to all of the businesses and individuals who contributed photos for this post.
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