When finding things to do in Portland, Maine, there is no one-size-fits-all itinerary. The Pine Tree State’s largest city is filled with maritime history, waterfront trails, numerous artisan shops, award-winning restaurants, and craft breweries.
As a lifelong Mainer and former Portland resident, I recommend a few things to keep in mind when planning your trip. First, make sure you have comfortable shoes and layers (even on the hottest summer days, it’s refreshing at night).
Portland is basically divided into two parts: the peninsula (where most of the recommendations below are located) and the off-peninsula (which includes the suburbs and many residential areas). If you stay primarily on the peninsula, walking, cycling, taxis and public transport are all options. If you want to explore the outskirts of town, you’ll probably need a car. Parking can be complicated, especially during peak travel periods, so it’s best to choose a hotel that offers parking, such as The Francis, which is free for guests.
From historic trails to island tours, here are 18 things to do in Portland, Maine.
Walk along the East Promenade.
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For a classic waterfront stroll, start from downtown Portland along the Eastern Promenade Trail. This two-mile trail is one of several in the park of the same name, designed by the famous Olmsted Brothers in the early 1900s. Along the way, watch the many migratory birds resting here, and stop for a snack at the food truck in the Cutter Street parking lot. East End Beach (more rocky than sandy) is a scenic spot to take in views of Casco Bay or rent a kayak to enjoy a different perspective of the city. If you want to explore further, access the Back Cove Trail and Bayside Trail from the boardwalk.
Enjoy the view from the Portland Observatory.
Get a 360-degree panorama of the city from the top of the 86-foot Portland Observatory. You can climb his seven steps at your own pace, or request a guided tour to learn more about the building’s heritage. This tower was built in the early 1800s and is the only remaining historic maritime signal station in the United States. Open from late May to early October, it’s run by the nonprofit organization Greater Portland Landmarks, which also offers walking tours of Portland’s various neighborhoods.
Enjoy a drink at Luna Rooftop Bar.
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The Canopy by Hilton enjoys a prime location on Portland’s waterfront, and its rooftop bar and restaurant, Luna, has become a favorite among hotel guests and locals since opening in 2021. Masu. Enjoy light snacks and artisanal cocktails while enjoying panoramic views of the harbour. From the observation deck on the 6th floor. If you book a stay at the hotel, don’t miss the pastries and specialty lattes at the Salt Yard, located on the street level.
Visit The Press Hotel’s art gallery.
The Press Hotel, located in the former headquarters of the Portland Press Herald, is one of Maine’s premier luxury hotels. Even if you’re not staying here, it’s worth stopping by the art gallery on the lower level of the property. It’s open to the public and spotlights the state’s up-and-coming and established creators. Enjoy a drink in the lobby’s bar, which features 62 vintage typewriters and pays homage to the glory days of journalism.
Check out events at Thompson’s Point.
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Thompson’s Point is a one-stop destination for entertainment, children’s museums, and special events year-round (there’s even a skating rink in the winter). In the summer, the venue offers free live music at sunset, hosts ticketed concerts in partnership with the State Theater, and also offers a wide variety of food trucks and places to enjoy beer, wine, and coffee. will be done. On select Sundays, the restored railroad depot hosts a Makers’ Market, where you can shop for local artisan creations while sipping a mimosa at the bar.
Go on a brewery tour.
With a craft beer scene like Portland, it’s impossible to choose just one brewery to visit. Maine Brews Cruises offers walking and bus tours that take you behind the scenes at the city’s pubs and breweries. Those looking to experience Portland’s breweries on their own time can check out the Maine Brewers Guild’s Route His Planner to create their own personalized itinerary and map.
Eat tacos at Bird & Co.
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Many tourists rave about Maine’s fresh seafood (and rightfully so), and this taco joint is one to look forward to. Thankfully, the 12 tacos are sold individually. Because with the creative menu, you’re likely to end up ordering one (or close to it) of each. Vegan and vegetarian options are also delicious.
Admire masterpieces at the Portland Art Museum.
Whether you’re a museum buff or just looking for things to do on a rainy day in Portland, you can’t go wrong with a visit to Maine’s largest and oldest public art museum. Founded in 1882, the Portland Art Museum features a permanent collection and special exhibitions of more than 19,000 of his works, including works by Andy Warhol and Claude Monet. The museum is spread across three of his architecturally stunning buildings in the city’s vibrant arts district and boasts a stunning sculpture garden. Check the calendar to see what’s happening or plan your visit around free admission times like Friday nights or the third Thursday of each month.
Take the ferry to Peaks Island.
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One of the best things to do in Portland (or anywhere in Maine) is to play in the water, especially in the summer. For just a few dollars each way, you can enjoy some sea air in 20 minutes to the islands of Casco Bay. Frequent ferry schedules make it easy to fit into your itinerary. On charming Peaks Island, find a secluded picnic spot, enjoy ice cream down the front or cinnamon buns from Peaks Cafe, or stop by the unique Umbrella Cover Museum. You can also rent kayaks and bicycles (although golf carts are the preferred means of transportation). For a long vacation away from the city, spend a night at The Inn on Peaks Island.
Shop at Black Box.
Located in the popular neighborhood of Washington Avenue, the Black Box is a series of repurposed shipping containers that provide small businesses with a physical space to operate. Current retailers include Moonday Coffee, Thicket Jewelry, Pinebury activewear, and more. This is an incubator space, so check out the website for the latest business.
Ride the Maine Narrow Gauge Railway.
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This family-friendly train takes you on a 40-minute ride along the Eastern Promenade with beautiful views of Casco Bay. Be sure to set aside time to explore the museum before and after your ride. In the summer, there’s the Ice Cream Train, where every passenger gets a cone, and in the winter, there’s the festive Polar Express, based on the popular Christmas movie.
Discover the hidden gems of Stevens Avenue.
The Dearing Center neighborhood has a little Stevens Avenue that you can’t miss. Drink coffee at Rwanda Bean, where 50% of profits go back to farmers. Next, check out The Honey Exchange to learn about beekeeping and peruse home goods, natural beauty and health products, honey-based products, and local beverages. Darby Jones is a boutique whose carefully selected products are “desirable non-essentials” and are a great alternative to typical souvenirs.
Taste fresh seafood at Luke’s Lobster.
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There’s a certain buzz and sense of place that comes with dining so close to a working waterfront. Watching fishermen haul in the day’s catch allows diners at Luke’s Lobster to connect their food with the local community. However, it’s not just the fresh seafood that is delicious. Luke’s Lobster has locations around the world, including his online Marketplace, and is proud of its sustainable practices and certified B Corp status.
Listen to live music.
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Portland attracts a wide variety of musicians and artists, and has multiple venues for performers. Portland House of Music, One Longfellow Square, State Theater, Blue, and Merrill Auditorium are some of the most popular spots to enjoy concerts.
Enjoy lobster on a Lucky Catch Cruise.
Experience a day in the life of a lobsterman with Lucky Catch Cruises, which offers interactive tours focused on Maine’s most important food export. On his 90-minute tour around Casco Bay, you can try your hand at trap pulling and enjoy beautiful views of the coast, historic forts, lighthouses, and more. After your cruise, buy lobster at wholesale prices. The restaurant next door, Portland Lobster Company, is happy to cook up your catch.
Stroll through the cobblestone streets of the Old Port.
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Old Port is a corner of downtown Portland with 19th-century red brick buildings, trendy boutiques, bars, restaurants, nightclubs, and live entertainment venues. Even as Portland’s population soars from 66,000 to more than 2 million in the summer, this part of the city retains a quaint atmosphere. Combine your visit with a Portland Schooner Company cruise, which offers a two-hour windjammer cruise around the bay.
Visit Maine’s oldest bookstore.
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Founded in 1886, Sherman’s Maine Coast Book Shop has several locations around the state, including one on Exchange Street in downtown Portland. Here you can find books by local authors and books on his list of best sellers. Sherman’s also sells gifts, toys, and a variety of Maine-grown specialty items.
Grab a bite to eat at The Porthole.
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Yes, it will be crowded, but The Porthole is one of the must-do experiences in Portland. This hole-in-the-wall restaurant opened on the waterfront in 1929 for fishermen to refuel in the early morning hours before heading out for a hard day’s work. May I recommend lobster Benedict for breakfast and baked stuffed haddock for dinner?
