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

When it comes to visiting Portland, Maine, there's only one thing you need to remember: There's no way to do it wrong.

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 a brisk night). Parking can be complicated, especially during peak travel months, so you may want to pay for hotel parking (The Francis offers it for free). Or, consider renting a car.

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 plan to mainly stay on peninsula.

Here are 18 of the best things to do in Portland, Maine.

Eastern Promenade

For those looking for a quiet walk outside the city center, the Eastern Promenade is a two-mile harbor-side stroll where you can grab a bite from the food trucks serving a variety of cuisines. Portland's food truck scene is robust, with approximately 70 set up within the city limits on any given day. 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. Meanwhile, kids will love the playgrounds.

Portland Observatory

For a 360-degree view of the city, visit this historic 86-foot tower where 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 observatory is run by the nonprofit Greater Portland Landmarks, which can set up travelers with walking tours of various Portland neighborhoods as well.

Luna Rooftop Bar

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 cocktails await with a panoramic view of the waterfront 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.

The Press Hotel

If you have a thing for old typewriters or simply want to visit a building that celebrates art in all forms, stop into The Press Hotel for a beverage and board game. You can also explore the lower level museum featuring Maine artists or type your own special something on the typewriter in the lobby.

Thompson's Point

Thompson's Point is a one-stop spot for concerts, a children's museum, special events, ice skating in the winter, and enjoying local brews, wine, food, and coffee. Plus, it's within walking distance of the Amtrak and Concord Coach Lines stations.

Portland Breweries

With a craft beer scene like Portland, it's impossible to pick just a couple of breweries to sample. The Maine Brews Crews offers various packages and tour options to ensure travelers get the ultimate brewery experience. For those wanting to experience Portland's breweries on their own time, this map is a convenient one to bookmark when building an itinerary.

Bird & Co. Tacos

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.

Cloudport CoWorking

With remote work making it easy for travelers to set up in their hotel room, snagging a day pass ($30) from Cloudport is a great way to mingle with Portland entrepreneurs and creatives while enjoying local coffee, beer, and wine from the self-serve taps. The central location is also within walking distance to all the local shops and restaurants, so you can enjoy sightseeing, shopping, and tasting once the workday is complete.

Ferry to Peaks Island

Getting on the water is a must when visiting Portland (or anywhere in Maine for that matter). For a few dollars each way (and a frequent ferry schedule that's bound to fit your itinerary), a 20-minute ride across Casco Bay will let you bask in the ocean air before pulling into the charming island town, where you can find a quiet picnic spot, enjoy ice cream from Down Front or a cinnamon bun from Peaks Cafe, and stop by a one-a-kind umbrella cover museum. Kayak and bicycle rentals are available (though golf carts are the preferred method of transportation). Spend the night at The Inn on Peaks Island.

The Black Box

Located on the popular strip of Washington Avenue, The Black Box is a series of repurposed shipping containers that provides small businesses with a physical space to operate. Current retailers include Moonday Coffee and Thicket Jewelry, North Optical, Alice Yardley, Fresh Pickins Farm, and Bay Bowls. Since this is an incubator space, check the website for the most up-to-date businesses.

Maine Narrow Gauge Railroad

In the summer, there's the Ice Cream Train, and come winter, families love booking rides on The Polar Express. This family-friendly activity takes passengers along the Eastern Promenade, offering scenic views of Casco Bay. Save some time to roam the museum before or after the ride.

Deering Center

There's a small stretch of Stevens Avenue in the Deering Center neighborhood that's not to be missed. To start, grab a coffee at Rwanda Bean, where 50% 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. Abura is your spot for relaxation and pampering, with massages, facials, and a collection of skin care products made on site. Darby Jones, a boutique that dubs its carefully selected wares as "desirable nonessentials," is a great alternative for typical souvenirs. Finally, wrap up your adventure by dining at Elsmere BBQ and Wood Grill, a neighborhood joint where you're sure to feel like a local.

Luke's Lobster

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 locations around the globe, including an online market, and it's proud of its sustainable practices and Certified B Corp status.

Dobrá Tea

For some introspection while traveling, visiting a traditional tea room like Dobrá can help recenter your busy body and connect you with your loved ones in a tranquil setting. Check the website for table tastings, workshops, and classes.

Live Music Venues

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.

Cobblestone Streets

The Old Port is a section of downtown Portland that's home to cobblestone streets, shops, bars, restaurants, nightclubs, and live entertainment. Even in the busiest of months, 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.

Sherman's Maine Coast Book Shop

Maine's oldest bookstore 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 speciality items.

The Porthole

Yes, it will be busy, but The Porthole is simply one of those places you have to experience in Portland. The restaurant opened in 1929 with the purpose of fueling fisherman 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?