Exploring the best things to do in Portland, Maine unveils a rich tapestry of activities that belie its small New England city status. Here, reinvention is rife, perhaps unsurprising given Portland had to rebuild itself following several devastating fires in the 18th and 19th centuries.
The spirit of that constant need to rejuvenate and rebuild means Portland has taken the best parts of its colonial and maritime history—historic docks, landmarks, Victorian houses and cobblestone streets—and melded them with more contemporary touches that have turned this little town into one of the hippest and most vibrant cities on the east coast.
Portland is home to excellent museums, great dining, a brilliant microbrewery scene, and a whole host of green spaces, so there is plenty to do both here and in the neighboring towns along the wider Maine coast.
Stroll Around the Old Port
Old Port
The history of Portland’s Old Port and its central thoroughfare, Commercial Street, is a checkered one. Dating from when the first settlers arrived in the 17th century, it was abandoned due to the French and Indian Wars. Once resurrected, it suffered destruction both in a British attack in the Civil War and a subsequent fire of 1866.
The port’s rebuilding in the 1870s led to much of what is seen today: historic docks, cobblestone streets, and red brick Victorian-era buildings mixed in with the occasional contemporary addition.
At its heart is the aforementioned Commercial Street. Created by landfill and running parallel to the waterfront, this thoroughfare is home to shops, bars, fine dining, and all manner of tour starting points, as well as a white granite marker dedicated to the Portland Freedom Trail.
Marvel at the Victoria Mansion
Victoria Mansion
At one stage, this elegant, 19th-century Italianate brownstone mansion sitting on leafy Park Street was penciled in for demolition, to be replaced by a gas station.
Originally built as a home for hotelier Ruggles Sylvester Morse, it was saved from that inelegant fate by William H. Holmes, who turned it into a museum in the early 1940s.
With interiors designed by the renowned Gustave Herter of Herter Brothers, it’s said that 97 percent of the original fixtures and fittings are still in place, including a smoking room that is one of the earliest examples of Islamic architecture in the country.
Now one of America’s National Historic Landmarks, the mansion offers a unique insight into upper-class life in the 19th century.
Take in the Views From the Portland Observatory
Portland Observatory
More than 200 years old and another National Historic Landmark, the Portland Observatory is the only surviving wooden signal station left in the United States.
Originally built in 1807 so that owner Captain Lemuel Moody could warn portside merchants that their ships were approaching the harbor, the 87-foot tower was rendered obsolete by the invention of the two-way radio in the 1930s.
Following a period of disrepair, it was opened to tourists in 1939 as an attraction with visitors able to climb the 103 steps to the viewing platform for 360-degree views of the city.
Enjoy Renowned Paintings at the Portland Museum of Art
Portland Museum of Art Photo by Paul VanDerWerf on Flickr, licensed under CC BY 2.0
Stretching from Deering Oaks Park to the waterfront is Portland’s High Street, a leafy promenade with the Portland Museum of Art at its midpoint.
Part of the thriving Arts District and spread across three buildings (two of which are historic and one designed by world-renowned contemporary architect IM Pei) its collection contains more than 22,000 works from the 18th century to today.
This is the largest collection of European art in the state, including works by Picasso, Munch, and Rodin. The Elizabeth B. Noyce Collection consists of 66 paintings and sculptures and offers masterpieces by Childe Hassam and Fitz Henry Lane.
Sip on a Locally Brewed Beer
Allagash Brewing Company
Maine is known for its craft beer, and lager lovers and ale aficionados will love a trip to Portland. The city and its surrounds claim to be the number one for breweries per capita in the United States.
While there are surely others that will contest the title, there are certainly enough microbreweries in town to ensure you never have to drink the same beer twice.
Popular breweries in Portland include the warehouse-like taproom of Bissell Brothers on Thompson’s Point, the rustic tasting room of the Allagash Brewing Company on Industrial Way, and the Shipyard Brewing Company, two blocks from the waterfront in the Old Port area.
Step Back in Time at Wadsworth-Longfellow House
Wadsworth-Longfellow House Photo by Brian Adler on Wikimedia Commons, licensed under CC0 1.0
Childhood home of the poet Henry Wadsworth Longfellow, who penned the famed Paul Revere’s Ride, this charming redbrick on Congress Street became a museum in 1902 after the passing of his last family member to live in the house.
Designated a National Historic Landmark in 1962, the museum, originally built by American Revolutionary War General Peleg Wadsworth in 1786, is said to be the oldest standing brick structure on the Portland peninsula. Exhibits include original fixtures, fittings, and furniture, plus there’s a research library, and fine gardens to explore.
Have Fun at the Children’s Museum & Theatre of Maine
Children’s Museum of Maine Photo by Chris Rycroft on Flickr, licensed under CC BY 2.0
Those visiting Portland with children need look no further than this long-standing museum with the sole aim of keeping younger visitors happy.
Born from the merger of the 1923 Children’s Theatre of Portland and the Children’s Museum of Maine, which dates from 1976, it is housed in a contemporary building on Thompson’s Point.
Interactive exhibits at the museum include a wet play area, a maker space, and indoor climbing walls, all spread over three floors, as well as Maddy’s Theatre that celebrated its centennial in 2023. A fenced-off outdoor play area is perfect for the sunny days of summer.
Read: Fun Things to Do in Maine With Kids
See Maine’s Oldest Lighthouse at Portland Head Light
Portland Head Light
Guiding sailors into Portland since the late 18th century, the Portland Head Light between Cape Cottage and Cape Elizabeth in South Portland is the oldest working lighthouse in the state of Maine.
Sitting just over 100 feet over the water and part of what is now Fort Williams Park, it consists of the tower itself (which is only open to the public on a single day every year) and the former keeper’s cottage. The latter houses an award-winning museum with informative exhibits, including a number of lighthouse lenses.
The surrounding 90-acre park offers picnic areas, hiking trails, historic forts, and sports fields, as well as incredible views over Casco Bay.
Read: Famous Lighthouses to See Around the World
Cycle the Eastern Promenade Trail
Eastern Promenade Trail
One of the best things to do in Portland, Maine is to enjoy the city’s oceanside location and maritime history by cycling the Eastern Promenade Trail on what was formerly a train track.
Starting at the Old Port and stretching for just over four relatively flat out-and-back miles, the trail mostly travels through Eastern Promenade Park for luscious ocean views.
Part of the East Coast Greenway that is hoped to one day connect Calais, Maine, with Key West in Florida, it passes by swimming beaches and picnic areas with benches. Those looking to extend their time on two wheels can prolong their adventures on the connecting Back Cove Trail.
Take to the Waves at Pine Point Beach
Pine Point Beach
The coastline around Portland is home to some incredible beaches in summer, with one of the best located some 15 miles south of the city, in Scarborough.
This seven-mile-long stretch of ice-white sand reaches from the jetty at Pine Point to Old Orchard Beach. You’ll find facilities including snack bars and restrooms here.
This Portland beach is a favorite with surfers thanks to the swells that roll in from Saco Bay. There are several shops offering rental gear to anybody who wants to ride the waves.
Jump on the Palace Playland Ferris Wheel
Palace Playland Ferris Wheel
Set on Old Orchard Beach just south of Scarborough, Palace Playground is a compact, old-school but fun amusement park, the only one in New England with an oceanside location.
Set over five acres, it is home to the largest arcade in Maine, offering vintage games and stalls, as well as 28 rides, from sedate offerings for kids to thrill-seeking ’coasters for adrenaline junkies.
Best of all, though, is the gondola Ferris wheel that offers spectacular views over the ocean and beyond.
Ride the Maine Narrow Gauge Railroad
Maine Narrow Gauge Railroad
Like many other narrow-gauge railroads in the United States, the rail line from Portland to Island Pond fell victim to financial troubles in the 1920s, and was mothballed until it was resurrected in 1993 as a tourist attraction.
The steam train takes passengers back in time in historic carriages on a 40-minute, three-mile round trip along Casco Bay from the Ocean Gateway Terminal, while conductors in period costume offer excellent historical commentary.
Departure times are hourly from 10 am to 3 pm, with special services including movie re-enactments, ice cream trains, and real ale journeys. There’s also an associated museum that tells the railway’s story.
Take to the Waters of Casco Bay
Casco Bay
Among all of Portland’s incredible history, it’s sometimes easy to forget that the Old Port is still a working harbor.
While many of the old fishing vessels may no longer be in action, taking to the water is easy enough. Various tourist boats and fishing charters offer trips from the port, while Casco Bay Lines has been offering a passenger, freight, and postal service to the bay’s main islands for more than 150 years.
Alternatively, there are a number of outlets offering everything from sailboat rental to surfboards and stand-up paddle boards (SUPs).
Hike the Trails of Mackworth Island
Mackworth Island
One place that visitors can reach without a boat is Mackworth Island. This 100-acre island with woodland, trails, and few buildings can easily be accessed from a causeway some five miles north of the downtown area.
Previously, it was the home of James Phinney Baxter and his son, Governor Percival Baxter. The island became part of the state in 1943. Now a bird sanctuary, there’s a 1.25-mile perimeter path through woods of spruce and pine, and past small, rocky beaches.
Birds that may be seen on the picturesque trail include Canada goose, American black duck, and ring-billed gulls. There’s also a small pet cemetery to the north of the island.
Read: Fall in Maine
Relax in Kennebunk & Kennebunkport
Kennebunkport
Some 30 miles south of Portland lies the quaint seaside town of Kennebunkport and its sister town, Kennebunk, further inland.
Set on the estuary where the Kennebunk River meets the sea, they offer quaint antique shops to explore, foodie tours, and miles of sandy New England beaches for swimming and boating.
Kennebunk also has a unique Museum in the Streets program over the summer season. This self-guided walking tour takes in 25 panels with rare photographs and documents from the town’s history.
See Vintage Automobiles at the Maine Classic Car Museum
Between Kennebunk and Scarborough lies this fascinating little museum, home to some 50 classic cars as well as hundreds of other exhibits from the golden era of motoring.
The collection features a number of unique cars, including a 1913 Model T, a Ferrari dating from 1968, President Roosevelt’s Packard, and a Tucker 48. The latter is widely considered to be a special collector’s item. Despite being one of the most innovative cars designed and built in the 1940s, only 51 were made before the Tucker Corporation was declared bankrupt.
The museum is also home to several works of art, including works by local artist Rod Williams, who produced illustrations for Ford and Chrysler. Those with deep pockets can also bag a rare souvenir: there are classic and rare car sales from the museum parking lot.
Walk the Presumpscot River Preserve
Presumpscot River Preserve
With some 70 miles of trails and 1,500 acres of parks, the area around Portland is one of the greenest urban areas in the United States. The surrounding regions are even better.
A great case in point is the Presumpscot River Preserve, a near four-mile wooden trail along the river which drains Sebago Lake to the ocean. The trail starts at Oat Nuts Park, following a deep ravine as it passes over boardwalks and bridges. It continues through the Falmouth Conservation Trust and the site of the former Smelt Hill Dam before reaching the powerful Presumpscot Falls.
Read: Best Places to Visit in New England
Portland
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