New England travelers looking to escape Boston need only to look north. There are some enjoyable, unique, and popular things to do in Portland, Maine, that locals love just as much as visitors.
As you spend a few more days in Portland, you’ll make other discoveries beyond the typical tourist path. The fun nightlife and art scene. A vibrant foodie and craft beer culture. Portland may be small in comparison to other capital cities, but it has a little slice of interest for all travelers.
Explore the Old Port District
The first stop for most travelers in Portland is the Old Port District, but you can’t forget about strolling on the Eastern or Western Promenade. Portland’s easy access to the ocean makes for a fun afternoon spent on the water, either by ferry, kayak, or paddleboard.
During the American Revolution in 1775, Portland, Maine, was destroyed by British naval ships, and the historic section of the city remains a time capsule of its original state, preserved as it was shortly after its reconstruction.
The city was a key port, and many battles took place during that time, which makes it a significant source of pride among locals.
Travelers from all over the world come to Portland to enjoy the historic cobblestone streets, 19th-century brick warehouses, and the preserved homes of prominent sea captains.
Visit the Portland Head Light
Portland Head Light is one of the most photographed lighthouses in the U.S. and is only a five-minute drive from the old port district.
The lighthouse is located in Port Elizabeth, a town situated on the southern border of Portland. It is best accessed via car, but travelers looking for a sustainable option can utilize the Gray Line, a hop-on/hop-off trolley service in Portland.
While at Portland Head Light, make sure to check out Goddard Mansion, a once-opulent, now-abandoned oceanfront mansion near the lighthouse.
Take a Ferry to the Casco Bay Islands
It’s no secret that one of the most popular things to do in Portland includes a visit to the nearby islands. Although the islands of Casco Bay are only accessible via ferry and don’t have a ton of road access once you get there, many of them are home to year-round communities that enjoy the remote life.
Outdoorsy visitors will love biking and hiking on Peaks Island, while Great Diamond Island boasts a quaint downtown area. Long Island boasts numerous stunning beaches.
Stroll the Eastern Promenade
About a 15-minute walk from the historic port district is another lovely section of Portland. True to its name, the Eastern Promenade is a long road and walking path on the east side of Portland.
Look left and you’ll see a quintessential New England neighborhood, look right and you’ll see a stretch of ocean. Occasionally, you’ll also catch a glimpse of the Maine Narrow Gauge train chuffing its way into downtown Portland.
Sip Your Way Through Portland’s Craft Beer Scene
Portland was taken over by hipsters, who then tapped into their entrepreneurial spirits and opened businesses. No wonder Portland, Maine, has a rather lively craft beer scene.
Favorited spots among locals include Allagash Brewing, Rising Tide, and Bissell Brothers. The breweries here often serve tasting flights on a seasonal rotation, accompanied by bar food and games.
Allagash hosts weekly trivia nights and live music events, and also offers interesting brewery tours for the inquisitive traveler. Grab your flannel and a pint glass, and you’ll fit right in.
Shop and Snack at the Portland Farmers’ Market
As a traveler, you can visit one of the oldest continuously operating farmers’ markets in the U.S., located in Deering Oaks Park.
Portland Farmers’ Market has been around since 1768—long before strolling through a farmer’s market became a popular weekend activity. In those days, markets served a more pragmatic purpose: to make a hard-earned living by selling produce, meat, and cheese.
And yes, the market in Portland has undergone a chic refresh since its early beginnings, but you can come here and witness a market true to its heritage—offering good, local, fresh produce for families who call Portland home.
Discover Local Art at the Portland Museum of Art
Although Boston usually takes the cake for having the best art scene in New England, you’ll find a tight-knit community of curators and makers in Portland.
In addition to some of the smaller artisanal shops in the historic port district, you can visit the Portland Museum of Art, the largest museum in Maine.
Works on display include those by Winslow Homer and Andrew Wyeth, as well as a rotating selection of exhibits featuring local and international artists.
Cruise on a Lobster Boat Tour
Maine lobster isn’t just for eating; it also makes for a great experiential travel experience. Maybe you never envisioned yourself as a weathered fisherman, but you can cosplay the lifestyle for a few hours in Portland.
Sign up for a morning fishing trip out in Casco Bay, where you’ll set lobster traps and learn from real fishermen. Lucky Catch Cruises has daily boat trips (weather permitting) where you’ll learn a ton about the lobster trade and cruise around the islands.
Try Portland’s Famous Food Scene
Aside from its booming craft beer scene, Portland is home to a fantastic foodie scene. In fact, many New Englanders (including myself) consider it our secret gem for local cuisine. Come here for a selection of James Beard–recognized restaurants and super fresh seafood pulled in from the bay.
Check out Eventide for a great selection of fresh oysters served on the half shell, or Scales for seaside dining (available for dinner and with a stunning view).
Plus, you can’t forget about sampling some of that famous Maine lobster. Check out Becky’s Diner for an unpretentious lobster roll.
Walk the Western Promenade
Situated on the opposite side of town is the Western Promenade, and, like all opposites, it has a totally different vibe than the Eastern Promenade.
Where the Eastern Promenade attracts joggers, dog walkers, and those who love a sweeping beach view, the Western Promenade is perfect for lazy sunsets. Come here for a walk or catch the occasional band playing on the lawn. You can even pull up a chair and enjoy a summer sunset.
Catch a Show at the State Theatre or Merrill Auditorium
The city offers a considerable amount of nightlife, and another popular activity in Portland includes catching a live performance.
Both the State Theatre and Merrill Auditorium are historic venues that host a wide range of musical performances, comedians, and plays throughout the year. If you plan to visit Portland in the fall or winter, when the nights are especially frigid, you’ll find many of the locals have turned these places into their hangouts before and after performances.
Explore Fort Gorges
Portland, Maine, played a significant part in the American Revolution, but has always been a prominent site for military action. Currently, there is an operating naval base in Portland, and a naval shipyard in the nearby town of Kittery, Maine.
For some more military history, hop on a boat to Fort Gorges, an island fortress that used to be a line of defense for Portland. You can also rent a kayak from the Eastern Promenade and arrive at Fort Gorges in about 20 minutes.
Conclusion
A visit here is an excellent experience of New England charm and hospitality. It’s a coastal gem that offers its own traditions and seasonal beauty. This is only one small part of a region that continues to be explored and loved for what it represents.