15 Best Things to Do in Portland, Maine, From Seafood Tours to Island Day Trips

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“15 Best Things to Do in Portland, Maine, From Seafood Tours to Island Day Trips”
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For such a little city, there’s plenty to keep you busy. 

March 25, 2022
15 Best things to do in portland maine From Seafood Tours to Island Day Trips

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Courtesy Portland Schooner Co.activity
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Portland Schooner Co.Arrow

Boarding one of these three schooners, all of which are on the National Register of Historic Places, is a terrific and different way to see Portland. It’s also fantastic for kicking back while discovering how beautiful Casco Bay is, with fresh, salty air all around you. For anyone who appreciates the above (as long as your stomach doesn’t do flips on the water), consider a sail with Portland Schooner Co. your one-and-done mode of exploration. 
Portland Freedom Trail
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Portland Freedom TrailArrow

A free and self-guided tour (no tickets required), the Portland Freedom Trail winds past 13 key sites celebrating 19th-century Black Mainers who fought to end slavery. It spotlights places along the local Underground Railroad used to secretly move formerly enslaved people into Maine and across the border to Canada (a crossing that signaled freedom). Included along the trail are other important historic abolitionist monuments, from the wharf, where many enslaved people stowed away on vessels to Maine, to churches-turned-meeting houses, private homes (with hidden passageways), and businesses that cleverly included anti-slavery pamphlets in their products.
  • Portland Museum of Art
    Erin Little/Courtesy Portland Museum of Artactivity

    Portland Museum of ArtArrow

    Founded in 1882 as The Portland Society of Art, this is the oldest public art institution in the U.S. That said, it’s relatively small and unassuming—more of a boutique museum, really. It’s spread over three interconnected, architecturally significant buildings: one modern building designed by I.M. Pei; one Federal-style, three-story mansion built in 1801; and one Beaux-arts style gallery built in 1911. It’s home to pieces from giants like Andy Warhol and Claude Monet, and significant collections of paintings by Wyeth, Homer, and Edward Hopper.
Portland ME Munjoy Hill
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Munjoy HillArrow

Both a jolt of energizing creativity and a window to the city’s history, this neighborhood is spread across the high ground at Portland’s east end. It was one of the first areas of Portland to be settled in the 1630s, and for centuries was home to working-class immigrants who made their livings on the waterfront—with an image of being a rough-around-the-edges but close-knit community. Then the ‘90s hit, along with an influx of artists and a burgeoning restaurant scene that brought new condos, art galleries, funky boutiques, and lively eateries to the area. Now, it’s also got the city’s best view at the Portland Observatory, those same fun shops, and award-winning restaurants like Terlingua. It’s the crossroads of historic Portland and the cool, contemporary side of the city. 
Portland ME Portland Head Light
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Portland Head LightArrow

Dating back to 1791, this is the oldest lighthouse in Maine and arguably the most beautiful in New England. It contains an excellent museum (in the former Keepers’ Quarters) delving into its history, as well as a gift shop. Just outside is Fort Williams Park, made up of 90 acres filled with coastal hiking paths and picnic tables, gardens, and a beach. Note that the park is open year round from sunrise to sunset, but the museum and shop are open daily in the summer, and weekends only during the off-season.
Portland ME Old Port
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Old PortArrow

When visitors think of Portland, it’s Old Port’s salty-aired, cobblestone streets and wharves that come to mind. Lined with boutiques and art galleries that alternate between posh and funky, 19th-century brick buildings, and some of the city’s best restaurants and bars, it’s a neighborhood that melds the cool and the quaint. In summer, Old Port is packed with tourists here for a sail with Portland Schooner Co., to check out the shops and world-famous restaurants, to visit the neighboring Casco Bay islands, or stroll the working harbor. Crowds thin out in the fall and become all but nonexistent in the winter, which is when locals reclaim the streets, and come out to dine and bar-hop themselves every evening.
  • Maine Foodie Tours The Shop Exterior
    Visit Portland/Kirstie Archambaultactivity

    Maine Day Ventures: Portland Old Port Culinary Walking TourArrow

    The flagship among all of Maine Day Ventures’s (formerly Maine Foodie Tours) offerings is this food tour that spotlights the ever-changing group of eateries and breweries that have helped put Portland’s working waterfront area on the map. Expect to sample everything from fresh lobster rolls to local craft beer (try Gritty’s), Maine crabmeat maki rolls, potato donuts (from Holy Donut), and creative superfood smoothies (at Blake Orchard). Some of the included spots are expected (you simply can’t tour in Old Port without at least a few spoonfuls of chowder) but and others surprising (chocolate truffles made from Aroostook County potatoes, for example). Above all, the storytelling and interactions are solid; guides do a good job of providing wide-ranging context for how foods are made and how they fit into the culture of the city.
Portland ME Bug Light Park
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Bug Light ParkArrow

Also known as Portland Breakwater Light, Bug Light (nicknamed for its small size) sits on the cusp of Portland Harbor and affords sweeping views of the city skyline. The expansive view of Portland and its working harbor dominates, with Munjoy Hill, Fort Gorges, and a handful of Casco Bay islands in the background. It’s set against about nine acres of maintained and manicured parkland, which residents use for picnics, boating, fishing, and kiting. Lighthouse lovers could easily spend hours just examining the 1875 structure’s decorative Corinthian columns alone.
Portland ME Portland Farmers' Market
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Portland Farmers’ MarketArrow

Supporting local agriculture has been a part of Maine’s way of life for as long as anyone can remember, and Portland’s farmers’ market is one of the best places to embrace that mission. Here 40-plus growers, cheesemakers, beekeepers, berry farmers, bakers, wildflower florists, and far more set up stalls twice a week in the summer and fall (Saturdays at the Deering Oaks Park location, and Wednesdays at Monument Square) and once a week during winter (Saturdays on Stevens Avenue).
Portland ME Allagash
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Allagash Brewing CompanyArrow

The vibrant craft beer movement in Portland may not exist without Allagash. It’s such a power player that the industrial park it calls home has turned into a brewery incubator of sorts, serving as a breeding ground for more than a half dozen Portland breweries, many of which have gone on to great success. The beer that made Allagash famous is its White—founder Rob Tod’s version of a Belgian wheat beer—which has become the de facto light beer for IPA lovers around the country. But Allagash does many things well, and whatever your beer proclivities, you’ll find something you’ll enjoy here. 
  • Summer Sunset truck
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    Thompson’s PointArrow

    Nature meets culture at this open-air entertainment venue on the Fore River, surrounded by three acres of picnic-ready lawn. The space, with its industrial-cool restored railroad shed, partners each summer with the State Theatre of Portland to host big-name concerts (everyone from Bob Dylan to Modest Mouse and The Lumineers). The rest of the year it brings in festivals: In summer, its “Maker’s Market” events are a Valhalla for those who yearn to shop artisanal, with an onsite bar in easy reach. In winter, there’s a well-tended skating rink that’s part family recreational center, part all-day, grown-up party. Whatever time of year or activity you come for, don’t neglect the epicurean attractions on the periphery, either: Thompson’s Point has a long track record of luring the most incredible food trucks in Southern Maine. 
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The Arts DistrictArrow

The Arts District is more a deep dive into the diversity of creativity in and around Portland than it is a single experience. It’s a neighborhood that encourages and celebrates artistic expression—from performances on stages and sidewalks, to abstract garden sculptures in the Portland Museum of Art; to, even, small family exhibits of paper mâché in coffee shops. Taken as a whole experience, the area is an excellent window into the kind of independent thinking that makes Portland tick, and is worth a look for anyone curious about its cultural mindset. If you can, time your trip to the first Friday of the month when, from 5 p.m. to 8 p.m., tourists and locals alike arrive to take part in First Friday Art Walk, a self-guided tour of the area’s arts offerings.
Eastern Promenade Portland Maine
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Eastern PromenadeArrow

Portland’s water views are at their most glorious in this 68.2-acre historic public park, where the city harbor and Casco Bay are the backdrop to walking and running trails—wooded and paved—dog walking, to boat launches, high-energy tennis matches, picnics, and relaxed beach days. It’s an easy-to-access, well-kept, splendid playground for all kinds of revelers, and one of the finest ways to experience what makes Portland such a special city.
Lucky Catch Cruises Portland Maine
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Lucky Catch CruisesArrow

Let the ultra-squeamish stay home; this 90-minute seafaring tour delivers a fun, hands-on understanding about one of New England’s most important industries: lobstering. It’s a fascinating educational mini-journey into the heart of Maine culture, and an up-close look at where one of the country’s most prized foods comes from. Run by a tight-knit company of lobstermen and their friends and crew, these excursions are designed to offer a first-hand glimpse into the daily routine of catching lobster. These guys are the real deal; when not bringing passengers along, they’re indeed out there on the waters, hauling in their traps. 


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