18 Best Things to Do in Portland, Maine, According to a Local (2024)

When it comes to finding things to do in Portland, Maine, there's no one itinerary that fits all. The Pine Tree State's largest city is filled with maritime history, waterfront trails, and a slew of artisanal shops, award-winning restaurants, and craft breweries.

As a lifelong Mainer and former Portland resident, I can recommend a few things to keep in mind when planning your trip. For starters, pack some comfortable shoes and layers (even the hottest of summer days come with brisk nights).

Portland is essentially divided into two parts: on-peninsula (where the bulk of the following recommendations are located) and off-peninsula (including the outskirts and many residential neighborhoods). Walking, biking, taxis, and public transportation are all options if you mainly plan to stay on the peninsula. If you want to explore the outskirts of town, you'll likely need a car. Parking can be complicated, especially during peak travel months, so you may want to choose a hotel that offers it (such as The Francis, where it's free for guests).

From historical trails to island excursions, here are 18 of the best things to do in Portland, Maine.

Walk along the Eastern Promenade.

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For a quintessential waterfront stroll, set off along the Eastern Promenade Trail from downtown Portland. The two-mile path is one of several in the park of the same name, designed by the renowned Olmsted Brothers in the early 1900s. Along the way, look out for the many migratory birds that make a rest stop here, and grab a bite from the food trucks in the Cutter Street parking lot. The East End Beach (which is more rocks than sand) is a scenic spot to take in the views of Casco Bay or rent a kayak for a different perspective of the city. If you want to explore further, the promenade links to the Back Cove Trail and Bayside Trail.

Enjoy the view from the Portland Observatory.

Get a 360-degree panorama of the city from atop the 86-foot-tall Portland Observatory. You can climb the seven flights of stairs at your own pace or request a guided tour for a deeper dive into the legacy of the building. The tower, which dates from the early 1800s, 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 Greater Portland Landmarks, which also offers walking tours of various Portland neighborhoods.

Have a drink at Luna Rooftop Bar.

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The Canopy by Hilton has a prime location on the Portland waterfront, and its rooftop bar and restaurant, Luna, has become a favorite among hotel guests and locals since it opened in 2021. Small bites and artisanal co*cktails await with a panoramic view of the harbor from the sixth-floor vantage point. If you happen to book a stay at the hotel, don't miss the pastries and specialty lattes at Salt Yard, located on the street level.

Visit the art gallery in The Press Hotel.

Housed in the former headquarters of the Portland Press Herald, The Press Hotel is one of the best luxury hotels in Maine. Even if you're not staying here, it's worth popping by the property's lower-level art gallery, which is open to the public and spotlights the state's emerging and established creatives. Stick around for a beverage in the lobby bar, which pays homage to the glory days of journalism with an installation of 62 vintage typewriters.

Check out an event at Thompson's Point.

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Thompson's Point is a one-stop spot for entertainment, a children's museum, and year-round special events (it even has a skating rink in the winter). In the summer, the venue offers free live music at sunset and ticketed concerts in partnership with the State Theatre, as well as a wide selection of food trucks and places to grab a beer, wine, or coffee. On select Sundays, the restored railroad shed hosts the Maker's Market, where you can shop for pieces from local artisans while sipping mimosas from the bar.

Go brewery hopping.

With a craft beer scene like Portland, picking just one brewery to visit is impossible. The Maine Brews Cruise offers behind-the-scenes walking and bus tours of the city's pubs and breweries. Those wanting to experience Portland's breweries on their own time can check out the Maine Brewers' Guild's route planner, which allows you to build a personalized itinerary and map.

Eat tacos at Bird & Co.

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While many visitors have their taste buds set on fresh Maine seafood (and rightly so), this taco joint should not be skipped. Thankfully, the 12 taco varieties are sold individually because the creative menu will likely have you ordering one of each (or close to it). Vegan and vegetarian options are deliciously celebrated, too.

Admire masterpieces at the Portland Museum of Art.

Whether you're a museum lover or simply looking for things to do in Portland on a rainy day, you can't go wrong with a visit to Maine's largest and oldest public art institution. Founded in 1882, the Portland Museum of Art features temporary exhibits and a permanent collection with over 19,000 works, including pieces by Andy Warhol and Claude Monet. The museum spans three architecturally stunning buildings in the city's vibrant Arts District and boasts a great sculpture garden. Check out the calendar to see what's on, or plan your visit around the free admission times, including Friday evenings and every third Thursday of the month.

Take the ferry to Peaks Island.

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One of the best things to do in Portland (or anywhere in Maine, for that matter) is to get out on the water — especially in the summer. For a few dollars each way, a 20-minute ride to the islands of Casco Bay will let you bask in the ocean air, and the frequent ferry schedule makes it easy to fit into your itinerary. On the charming Peaks Island, you can find a quiet picnic spot, enjoy ice cream from Down Front or a cinnamon bun from Peaks Cafe, and stop by the one-a-kind Umbrella Cover Museum. Kayak and bicycle rentals are available (though golf carts are the preferred method of transportation). For a longer getaway from the city, spend the night at The Inn on Peaks Island.

These Little-known Islands in Maine Offer a Charming Getaway — With Delicious Seafood and Picturesque Views

Shop at The Black Box.

Located on the popular strip 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, and Pinebury activewear. Since this is an incubator space, check the website for the most up-to-date businesses.

Ride the Maine Narrow Gauge Railroad.

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This family-friendly railway takes passengers on 40-minute train rides along the Eastern Promenade with scenic views of Casco Bay. Save some time to roam the museum before or after the ride. In the summer, there's the Ice Cream Train, where every passenger gets a cone, and winter brings the festive Polar Express, based on the popular Christmas movie.

Discover hidden gems on Stevens Avenue.

There's a small stretch of Stevens Avenue in the Deering Center neighborhood that's not to be missed. Grab a coffee at Rwanda Bean, where 50 percent of the profits go back to the farmers. Then, check out The Honey Exchange to learn about beekeeping and peruse some home goods, natural beauty and health products, honey-based items, and local beverages. Darby Jones, a boutique that dubs its carefully selected wares as "desirable nonessentials," is a great alternative for typical souvenirs.

Chow down on fresh seafood at Luke's Lobster.

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There's a certain buzz and sense of place that comes with dining within arm's reach of a working waterfront. Seeing the fisherpeople pull up with the day's catch connects diners at Luke's Lobster with their meal and the local community. But it isn't just the fresh seafood that's to be celebrated. Luke's Lobster has outposts around the globe, including an online market, and it's proud of its sustainable practices and Certified B Corp status.

The Best Times to Visit Maine for Lower Prices, Smaller Crowds, and the Tastiest Lobster

Catch some live music.

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Portland attracts an array of musicians and artists, and is home to multiple venues for performers. Portland House of Music, One Longfellow Square, State Theatre, Blue, and Merrill Auditorium are among the most popular spots to enjoy a concert.

Go lobstering with Lucky Catch Cruises.

Experience a day in the life of a lobster fisher with Lucky Catch Cruises, which offers interactive excursions focusing on Maine's most important food export. During the 90-minute tour around Casco Bay, you can try your hand at hauling up the traps and enjoy the scenic views of the coast, historic forts, and lighthouses. After the cruise, purchase some lobster at the wholesale price — the restaurant next door, Portland Lobster Company,will happily cook your catch for you.

Wander the cobblestone streets of the Old Port.

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The Old Port is a section of downtown Portland that's home to 19th-century red brick buildings, cool boutiques, bars, restaurants, nightclubs, and live entertainment venues. Even when Portland's population soars from 66,000 to more than two million in the summertime, there's a quaint vibe to this part of the city. Pair your visit with a sail with Portland Schooner Co., which offers two-hour Windjammer cruises around the bay.

Stop by 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 in the heart of Portland on Exchange Street. Here, you can find books by local authors, as well as those on the bestseller list. Sherman's also sells gifts, toys, and a variety of Maine-made specialty items.

Grab a bite at The Porthole.

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Yes, it will be busy, but The Porthole is simply one of those places you have to experience in Portland. The hole-in-the-wall restaurant opened on the waterfront in 1929 to fuel fishermen early in the morning before they went out for a day of laborious work. May we suggest the lobster Benedict for breakfast and baked stuffed haddock for dinner?

18 Best Things to Do in Portland, Maine, According to a Local (2024)


What not to miss in Portland, Maine? ›

  • The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local. ...
  • Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour. ...
  • Harbor Lights and Sights Cruise. ...
  • Downtown Portland, Maine City and Lighthouse Tour-2.5 hour Land Tour. ...
  • Portland Tall Ship Cruise on Casco Bay.

What is Portland, Maine best known for? ›

Maine's prominence as a craft beer and wine destination continues to grow. Portland lays claim to 17 microbreweries—the most per capita of any city in the nation, according to the Brewers Association. Allagash Brewing Company in Portland produces 45,000 barrels of beer each year.

What is the nicest part of Portland Maine? ›

West End. Besides the Old Port, The West End is one of the most charming places in Portland. The architecture is amazing. Parking can be quite tricky on the West End.

Is there a lot to do in Portland, Maine? ›

There's always something to do in Greater Portland, Maine.

From daily tours to cruises, art exhibitions, music, and live performances. Browse our Events Calendar and save your favorites. Always cross-check event time/date with organizer's website before booking.

Is it safe to walk downtown Portland Maine? ›

According to US News and World Report, “Maine has one of the lowest crime rates in the country, and crime rates in Portland are lower than average for a metro area of its size.” Your biggest danger is slipping on ice, a sidewalk brick, or treading on dog poop.

What food is Portland most known for? ›

While Portland doesn't have a single iconic food, like cheesesteaks in Philadelphia or clam chowder in Boston, it has a number of must-taste delicacies. The Maple Bacon bar at Voodoo Doughnuts, the Reggie Deluxe at Pine State Biscuits and khao man gai at Nong's usually make the top of the citywide best-of lists.

What is the nickname for Portland Maine? ›

STUMPTOWN - this name has gained national notoriety with the proliferation of the eponymous coffee roaster but few people outside of the state know that this is a nickname for Portland.

What foods is Maine famous for? ›

Maine is not only known for its lobsters and blueberries but also for its oysters. The Pemaquid Oyster Festival takes place in Damariscotta Maine every September. Here, you can indulge in freshly shucked oysters and witness live demonstrations of oyster farming techniques.

What is the safest part of Portland? ›

The Pearl District stands out as one of Portland's safest and trendiest neighborhoods. This urban paradise boasts a low crime rate, making it a top choice for residents seeking a secure and stylish place to call home.

What is the coolest neighborhood in Portland? ›

Q: What is the coolest neighborhood in Portland? A: Nob Hill is the coolest Portland neighborhood on the west side of the river, thanks to its many trendy boutique shops, great restaurants and bars, and walkability. On the east side of the river, SE Hawthorne is generally considered the coolest or hip part of town.

What is the most walkable area of Portland, Maine? ›

Walk Score: 62

As the largest city in the state, Portland boasts several pedestrian-friendly neighborhoods like Old Port and Munjoy Hill. These areas contain a variety of shops, restaurants, and attractions easily accessible on foot. Discover Portland, ME homes for sale and apartments for rent.

What is the best month to visit Portland Maine? ›


Once the summer traffic clears, Portland becomes a lot quieter – making fall a great option for travelers who don't want to battle the crowds. September highs can reach 70 degrees, but once October hits, highs hover in the 50s before dipping to the 40s come early November.

How many days in Portland, Maine is enough? ›

How many days do I need to see Portland, Maine? For a comprehensive experience of Portland and its surroundings, plan a 5-day trip. You'll want to spend three days exploring the city's downtown area, coffee shops, local breweries, and amazing restaurants. Reserve the other two days for day trips to nearby attractions.

How many days in Portland is enough? ›

You can see many of Portland's most popular attractions in two to three days if you stay in or near downtown. If you'd like to visit Mount Hood, hike in the Columbia Gorge, visit the Oregon Coast, or see how locals live by spending time in one of Portland's many neighborhoods, we recommend at least five days.

What area to avoid in Portland Downtown? ›

With a crime rate that is 228% above the national average, Powellhurst is a dangerous Portland neighborhood that is best avoided. A large homeless population contributes to the rampant property crime, drug use, and unsanitary conditions in the area.

What area in Portland or to avoid? ›

Located in the heart of downtown Portland, Old Town/Chinatown has historically experienced higher crime rates due to its concentration of bars, homeless services, and nightlife. While efforts have been made to improve safety, incidents related to property crime and public disorder have been prevalent.

How many days do you need in Portland, Maine? ›

How many days do I need to see Portland, Maine? For a comprehensive experience of Portland and its surroundings, plan a 5-day trip. You'll want to spend three days exploring the city's downtown area, coffee shops, local breweries, and amazing restaurants. Reserve the other two days for day trips to nearby attractions.

What is unique about Portland? ›

1. Portland is home to the word's smallest park. Mills End Park, located near the Willamette River in downtown, is recognized by the Guinness Book of Records as the smallest park in the world. The grassy area has a diameter of 0.6 meters and a total area of 0.29 square meters.

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