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The Top 10 Things to Do and See in Bayside, Portland

The Top 10 Things to Do and See in Bayside, Portland

Picture of Prachi Vyas
Updated: 9 February 2017
East Bayside is Portland’s proprietor of an off-brand Maine culture. Steeped in cultural richness and historical significance, you’ll feel rejuvenated by the end of your trip. If you’re curious about art, there are places to go where you can observe and create. If you’re looking to unwind against the sound of crashing waves, Bayside has unique access to the shoreline. Restful yet restless, it has something for every kind of traveler.

Back Cove Trail

No matter which season is upon you, there will be something to see at Back Cove Trail. One of the most popular Portland Trails, the three-and-a-half mile stretch edges along the Back Cove shoreline. Just on the outskirts of the Bayside neighborhood, the picturesque footpath is ideal for biking, running, bird-watching or just taking a stroll. There’s more to the view than the city skyline: you’ll catch glimpses of lovely Bayside neighborhoods, local parks and the backside of Portland.

Address and telephone number: 305 Commercial Street Portland, ME 04101 +1 207-775-2411


If neither running nor jogging appeal to your sportive style, consider biking with Cyclemania through the winding streets of Bayside. The skilled guides are receptive and friendly, pulling over every now and then so you can catch your breath or check out an interesting eatery. Each day of the week offers a unique program that targets different levels of biking expertise. Mondays are great for new riders and as light physical therapy while Tuesdays are perfect for advanced riders who are up for the challenging 48.5-mile trek.

Address and telephone number: 65 Cove St., Portland, Maine +1 207-774-2933

Take a self-guided “foodie” tour

Stuff yourself with beer and treats that you can’t get anywhere else by taking yourself on a self-guided “foodie” tour of Bayside. The checklist, created by the local culture magazine Maine Today, features rebellious coffee blenders, flavorful palm-sized pies and holistic herbal elixirs. Maine is also rapidly becoming a haven for microbreweries that appeal to the craft beer lover in you, and Bayside has one of the best: Maine Craft Distilling, the second stop on the food tour. Don’t worry about getting lost – almost everything on the list is on Fox Street, a popular Bayside strip.

Portland Stage Company

Its tagline asserts “Maine’s Premier Professional Theater,” and the folks at Portland Stage Company make sure their shows deliver. The most recent one, “Papermaker”, just wrapped up its season in May after months of sold-out shows and accolades for local novelist-turned-playwright Monica Wood. The interior is decorated like an old-fashioned theater, with a red velvet-covered staircase that connects the two always-packed floors. The next season, opening this September, will showcase Brian Friel’s “Dancing at Lughnasa” and the tickets are already on sale – check the website for more information.

Address and telephone number: 25 Forest Ave., Portland, ME 04101 +1 207 774 0465

Bayside Bowl

Bayside Bowl is the preferred hangout spot of Bayside’s youthful crowd, but rest assured you’ll find all kinds of bowlers here: from first-timers learning just how heavy bowling balls are to seasoned bowlers who get strike after strike. This high-tech arena boasts an upbeat atmosphere, great music and a delicious diner where you can get gourmet burgers and crispy fries. Whether you’re on a date or you’re spending time with friends, Bayside Bowl is a fun way to end or begin your night.

Address and telephone number: 58 Alder Street, Portland, ME 04101 +1 207-791-2695

Portland Flea-for-All

If you’re in the mood for some shopping but your budget is tight, head over to Portland Flea-for-All. An eclectic indoor flea market in the heart of Bayside, it embodies the funky and unconventional artsy vibe that now runs freely throughout the neighborhood. The booths almost exclusively feature local artists selling jewelry, prints, housewares, furniture and more. You will never see the same item twice, and might just find something perfect.

Address and telephone number: 125 Kennebec St, Portland, ME 04101 +1 207-370-7570

Wadsworth-Longfellow House

Literary buffs rejoice: the historic Wadsworth-Longfellow House is now a public museum, open to those who wish to see how poet Henry Wadsworth Longfellow lived in his youth. Because nearly every relic in the house has been perfectly preserved, people often describe the experience as taking a step back in time from the moment you step inside. From using candlelight to illuminate rooms to the use of the Wadsworth-Longfellow family’s original furniture, everything about this home-turned-museum is truly authentic. And, the cherry on top of any good museum, this one comes with a well-stocked gift shop too.

Address and telephone number: 489 Congress St., Portland, ME 04101 +1 207-774-1822

Portland Symphony

In a town where everything is unconventional and contemporary, it’s nice to have a place like Portland Symphony, where you can enjoy classical music at your leisure. The Portland Symphony is a Bayside establishment that pays homage to masterpieces, featuring artistic skills of the highest caliber. Their musical menu varies from season to season but usually offers a range of ballet shows, orchestra pieces, contemporary soloists and choir performances. The gorgeous interior enhances the elegant ambiance, with tiered seating and velour drop curtains that glow in the golden stage lighting.

Address and telephone number: 50 Monument Square, 2nd floor, Portland, ME +1 207-773-6128

Running With Scissors

If you love modern art and want to support local artists, then check out Running With Scissors: an art gallery full of pieces by local artists. Its experimental, innovate taste in works of modern expression is legendary in the artistic world and attracts quiet art lovers from all corners. Don’t let the idea of an art gallery turn you off: their artisans personally attend their showcases, proudly showing off their paintings, sculptures, jewelry and even polished beach stones from nearby Back Cove.

Address and telephone number: 250 Anderson Street Portland, ME 04101 +1 207-831-5682

Relax on the Back Cove shoreline

The Back Cove is a nearly circular basin on the northern side of Portland, and the trail mentioned above runs the circumference of the Cove. If you’ve tired yourself out from running in loops, take a picnic basket to the shoreline at evening and drink in the beautiful red-gold sunset on the estuary horizon. The natural loop-shape of Back Cove completely drowns out the loud sounds of the vibrant city, allowing a peaceful calm to take its place and internally converting visitors into lifelong Mainers.

Address: Back Cove, Portland, Maine

Prachi Vyas