25 Top-Rated Things to Do in Portland, ME

Portland is a charismatic city that offers visitors a wide variety of cultural attractions, as well as plenty of opportunities to get active. Known for its top-notch art museum and abundance of creative public murals and sculptures, this coastal city inspires visitors of all ages.

This harbor city also has a rich maritime history, active with fishing and trade long before Europeans claimed the land and used the protected Casco Bay for their huge ships. Portland, as well as its many offshore islands, has been home to numerous military fortifications that date back to the Revolutionary War, and many of these can still be explored.

While you can get to many of the downtown tourist attractions and things to do easily by foot, Portland is relatively spread out and quite hilly, so leave yourself time to take a break, and bring good walking shoes. Garage parking is at a premium here, and street parking is difficult to find, so you may want to consider using a taxi or rideshare service for jaunts across town–or at least for the uphill leg of the journey.

Whether you’re visiting for the history, the art, or the water, plan your adventures with our list of the best things to do in Portland, Maine.

1. Stroll Commercial Street’s Waterfront and the Old Port

The Old Port is the heart of Portland’s historic district, where the brick and stone of the grand old warehouses extends into brick-paved sidewalks and stone-paved streets. Although these streets are open to traffic, the area is dominated by pedestrians, so it’s best to park at a garage or on a side street and explore by foot.

Commercial Street is where you will find dozens of boutiques, from locally made goods and maritime-themed upscale souvenirs to clothing and specialty imports. You’ll also find an abundance of restaurants, from hot dog stands and grass-fed specialty burgers to seafood and fine dining.

If you brought your pole, head on over to the Maine State Pier and drop a line. Also home to the Casco Bay Lines ferry port, this wharf has plenty of space to stroll for excellent views of the harbor. Adults love seeing the schooners and fishing boats come and go, while kids love watching the giant cargo barges and adorable tugboats.

Insider tip: Although parking isn’t cheap anywhere in the city, avoid parking at any of the wharf lots off Commercial Street–they are outrageously expensive and have very strict time limits.

2. Cruise the Calendar Islands

The Casco Bay Islands have been referred to as the Calendar Islands for so long, the names are now interchangeable. They earned this nickname due to their number, and although there aren’t quite enough to make it true, the moniker stems from the claim that there are enough of them to visit a different one each day of the year.

Several of these islands are home to former military fortifications, like Fort McKinley on Great Diamond Island and Battery Steele on Peaks Island. Chebeague Island is home to a golf course that offers stunning views from its green, and working fishing vessels give Bailey Island an authentic down-east coastal feel.

There are several tour operators offering cruises to and around the islands. Portland Discovery Land & Sea Tours offers a good variety, including lighthouse tours, sunset tours, and private charters.

If you want to cruise in style, there are also plentiful options for sailing: the Portland Schooner Company offers three daytime sails and a sunset sail during the summer, and Maine Sailing Adventures offers a variety of sightseeing and specialty sails on the windjammer Frances.

If you’re in the mood to explore on your own, many of the islands can be reached via the ferry as well; the ferry is also a great way to get out on the water during the off-season, when most cruise tours have stopped running.

3. Take the Ferry to Peaks Island

Once known as the “Coney Island of Maine,” Peaks Island is now a far quieter spot than it once was, but it’s still a popular destination for those who enjoy the peace and simplicity of island life.

Part of the city of Portland, Peaks Island can be accessed easily and affordably via the Casco Bay ferry. Although the ferry does carry vehicles, don’t bother to pay the hefty fees to bring your car over–tourists can easily explore the island by foot, bicycle, or rented golf cart while avoiding the hassle of finding parking once there.

Peaks Island is full of interesting things to do, from quirky attractions like the Umbrella Cover Museum to fascinating historic military sites like Battery Steele. Nature lovers will want to spend hours exploring the trails and bird-watching in the Peaks Island Land Preserve, and there are countless spots to sit and simply soak up the views of the ocean and surrounding islands.

Savvy tourists can get an inexpensive tour of Casco Bay via the ferry, as well, with per-person rates starting at under eight dollars in the tourist season for a round-trip to Peaks. This jaunt across the bay takes about 17 minutes each way and gives you an excellent view of Portland from the water, as well as views of hard-to-reach attractions like Fort Gorges.

Those who want to see even more can hop the ferry to one of the other islands, or take the Mailboat Run for a 2.5- to 3.5-hour cruise that visits Little Diamond and Great Diamond, Long Island, and the Chebeague Islands. It costs only $17 (less for kids and in the off-season) and even turns into a narrated sightseeing cruise when there are more than 10 passengers–by far the most affordable way to cruise Casco Bay.

Ferry Landing Address: 56 Commercial Street, Portland, Maine

4. Take Pictures at Portland Head Light

Found along the entire coastline, Maine’s lighthouses have become an iconic symbol of the state. Their frequency is due to the sheer number needed to guide fishing and trade boats of all sizes as they approached the unpredictable coast long before other technologies were there to assist.

Portland Head Light on Cape Elizabeth is not only one of the most picturesque of Maine’s lighthouses, it’s one of the most accessible. This landmark can be easily reached by tourists who want to snap shots of its profile against the backdrop of Casco Bay, while enjoying the views of Portland Harbor and the islands.

You can also see the inside, where there is an excellent museum in the former Keeper’s Quarters. Tourists can learn about the lives of lighthouse keepers and technological advances over the centuries, and also view historic documents and artifacts from Portland’s earliest seafaring days.

Address: 1000 Shore Road, Cape Elizabeth, Maine

5. Visit Victoria Mansion

One of America’s most important residences of the Victorian period, Victoria Mansion is an outstanding example of the architecture and interior décor of the era. It is also exceptionally well preserved and maintained; you will be dazzled by the interior and by the carpets, furniture, porcelain, silver, fabrics, and other decorative items that fill the mansion.

Each room is more ornate and richly embellished than the last, from the painted walls and stained-glass windows in the Reception Room to the over-the-top Turkish Smoking Room, where not a single surface is left unadorned. The design themes and colors reflect the Moorish style of Spain’s Alhambra.

Even the richly paneled library, although it’s almost entirely in wood, is replete with elegant carving. Detailed plasterwork is used everywhere and often gilded to lend even more glamor to the rooms and give you a glimpse of the lavish lifestyles of prosperous families in the Victorian era. Remember that this was only a summer home!

Address: 109 Danforth Street, Portland, Maine

6. Explore the Eastern Promenade

The Eastern Promenade is actually home to three trails that run mostly parallel to each other along the waterfront in the East End of Portland.

The Eastern Promenade Trail is the longest section and closest to the water’s edge, starting in Portland’s Old Port district and then running along the edge of Fort Allen Park, past East End Beach, and ending at Bayside Trail by Tukey’s Bridge, for a total of 2.1 miles.

The Eastern Promenade itself occupies the interior track, running along the street of the same name from Fort Allen Park to the Major Charles Loring Memorial Park. The section is paved, making it accessible to wheelchairs and strollers, and is the access point for several community recreation areas.

The Midslope Trail sits where you would expect–along the slope between the other two–and offers connecting trails between all three for access to the water at many points. Tourists will find plenty of benches and picnic tables along each route, and in the summer, you’ll find a selection of good eats near the midpoint at the Eastern Prom Food Truck Park.

7. Soak Up Culture at the Portland Museum of Art

With so many world-class artists working or having worked in Maine, it is not surprising that Portland has an exceptional art museum. But the collections in the Portland Museum of Art go well beyond the works of Winslow Homer, Rockwell Kent, Edward Hopper, and the Wyeths.

Among the more than 18,000 pieces in the collections here are works by Monet, Degas, Picasso, O’Keefe, Cassatt, Renoir, Warhol, Stuart, Sargent, and Whistler. Outdoor sculptural works are by Robert Indiana and others. In addition to paintings and works on paper, the museum has collections of glass art that include several Tiffany pieces.

The fine and decorative arts date from the 1700s to contemporary pieces, focusing especially on American and European paintings.

Attached to the museum is the 1801 McLellan House, a three-story federal-style mansion, recently restored and displaying outstanding examples of period furniture, paintings, and decorative art.

A highlight of the collections is the more than 650 oil paintings, etchings, and watercolors by Winslow Homer. His studio at Prouts Neck is owned by the museum, and you can visit on tours originating at the museum (see below).

Admission to the Portland Museum of Art is free every Friday from 4pm to 8pm.

Address: Seven Congress Square, Portland, Maine

8. Take the Kids to the Children’s Museum & Theatre of Maine

The Children’s Museum & Theater of Maine is Portland’s top family attraction, full of fun and activity for babies, toddlers, and grade-school-aged children. In its new three-story, 30,000-square-foot facility, you’ll find plenty of space for kids to explore the exhibits and work off their extra energy within the interactive museum.

One of the most popular exhibits is Our Neighborhood, which occupies one full floor of the museum with a kid-sized town. Here, they can work at a doctor’s office, tend to the fire trucks, be both customer and vendor at a farmers market, and even play on a Maine lobster boat. The smallest visitors should check out Lighthouse Cove, which was designed with infants and toddlers in mind.

Climb, Crawl, and Slide is the museum’s indoor climbing space, perfect for toddlers and kids who love to explore. Aspiring performers can head to the Dress Up Theater to don costumes and act out their favorite stories, and guests can also see live performances here by more practiced actors.

Address: 250 Thompson’s Point Road, Portland, Maine

9. Hit the Beach at Crescent Beach State Park

Crescent Beach stretches along a mile of sandy shoreline on Cape Elizabeth, making Crescent Beach State Park a top summertime destination for both locals and tourists. The beach itself offers a good number of amenities during the summer, including a large changing and shower facility, a spacious shaded picnic area, a concession stand, and lifeguards.

If you’re visiting in the off-season, there is still plenty to do at the park, with boardwalks through the dunes and plenty of space for strolling on the beach. This is also a popular fishing spot, and sea kayak rentals are available on-site as well. If you stop by in the winter, you may even see cross-country skiers!

Address: Bowery Beach Road, Cape Elizabeth, Maine

10. Be on the Lookout at the Portland Observatory

Although the Portland Observatory looks like a lighthouse, it was actually constructed to give the land-based ship owners advance notice of their ship’s arrival so that unloading crews could be ready and waiting at the dock.

Constructed in 1807 by Captain Lemuel Moody, the observatory used high-powered lens telescopes to watch for incoming boats, with a range of spotting them up to 30 miles from shore. The service wasn’t free, of course, and local shipping crews used this tower’s services up until the two-way radio became standard in 1923.

The tower was added to the National Register of Historic Places, and re-opened in 1939 as a tourist attraction commemorating the Age of Sail. Today, you can tour the fully restored building and enjoy looking out from the observation deck to get your own perspective on ships in Casco Bay and beyond–as well as excellent panoramic views of the city below.

Visitors should be aware that the Observatory is only open during the summer tourist season, but tickets are available for pre-purchase online.

Address: 138 Congress Street, Portland, Maine

11. Get on Track at the Maine Narrow Gauge Railroad Co. & Museum

The Maine Narrow Gauge Railroad Museum is dedicated to preserving the history of the two-foot-gauge railway. It’s a big hit with kids and kids-at-heart, with plenty of exhibits and activities, as well as several historic coaches that you can explore.

If you are interested in seeing the Eastern Promenade but aren’t up to the walk, hop aboard the museum’s scenic train ride. This three-mile route skirts Portland’s East End for beautiful views of the bay and harbor, operating May through October multiple times per day.

From late November through Christmas, the train fires up again for a Polar Express ride, an excellent thing to do with kids if you’re visiting Portland during the holiday season. There are also seasonal and special theme rides throughout the year.

Address: 58 Fore Street, Portland, Maine

12. Relax at Fort Williams Park

Located in South Portland on Cape Elizabeth, Fort Williams Park is full of recreational activities, historic attractions, and scenic vistas. It covers 90 acres of coastal land and is most famous as the home of the iconic Portland Head Lighthouse, with multiple viewing points for stunning shots of the light.

One of the most popular things to do at the park is explore the many old military fortifications. Visitors will find outdoor displays with historic photos and information at Battery Blair, which also serves as an excellent vantage point for viewing the lighthouse.

Battery Keyes is another popular spot to explore, located at the northern end of the park beyond Battery Sullivan and Battery Hobart. A few steps away, you can explore the stone ruins of Goddard Mansion, where nature is slowly reclaiming the site, and trees peek out of old windows.

The Friends of Fort Williams offer garden and plant tours regularly from spring through fall, and there is a lovely Children’s Garden next to a small pond that makes the perfect place to visit for a picnic. There are also shaded picnic areas throughout the park.

To learn more about the fort’s history, stop at the museum located at Portland Head Light, on the park’s promontory; here, you will find exhibits and artifacts related to the fort’s active years.

Address: 1000 Shore Road, Cape Elizabeth, Maine

13. Delve into History at the Wadsworth Longfellow House

Just a block up the street from Monument Square, tucked between tall city buildings, sits an unassuming two-story brick house covered in crawling vines and skirted by an iron fence. Named a National Historic Landmark in 1962, the childhood home of this prolific poet is now under the care of the Maine Historical Society, which also offers exhibits in its facility next door.

Wadsworth Longfellow House has been well-preserved, and tourists will find that nearly all the household items and furniture on display inside are original to the home. This was, in fact, Maine’s first museum-home opened to the public, after the death of Anne Longfellow Pierce in 1901. It also has the distinction of being the first entirely brick dwelling in the city and the oldest standing building in Portland.

Visitors can take a guided group tour led by a Historical Society docent, or take a self-guided tour. Whichever you choose, be sure to leave time to explore the beautiful Colonial Revival garden that sits tucked away behind the building. The garden itself is free to visit May through October during museum hours.

Address: 489 Congress Street, Portland, Maine

Official site: www.mainehistory.org/house_overview.shtml

14. Explore Fort Allen Park

Located just north of the Old Port district, Fort Allen Park is the starting point for the Eastern Promenade. Although it only occupies 10 acres, there’s plenty to do and see here.

Originally the site of a Revolutionary War fort, the park now also has a Civil War monument, as well as a cannon from the USS Maine, which sank in 1898. There is also a beautiful memorial made from the mast of the USS Portland, a 9/11 Memorial, and the Arctic Memorial dedicated to the 3,000 people who lost their lives in the Arctic Campaign during World War II.

Throughout the park, visitors will find educational plaques that share facts and stories about the site’s history. The lovely gazebo is used as a bandstand; this is a popular picnic spot, where you can sit and watch the boats come and go from the harbor.

It’s also convenient to East End Beach, a small but popular Portland area beach that’s frequented by leashed dogs and their parents, as well as the East End Boat Launch. This is the best kayak launch spot in town, and you can fish from here as well.

Address: Eastern Prom Boulevard, Portland, Maine

15. Tour Portland on a Vintage Fire Truck

Bus and trolley sightseeing tours are one of the best ways to introduce yourself to a new city and get a feel for its layout. In Portland, you can do this in style by hopping aboard a vintage fire truck for a 50-minute sightseeing tour .

From the comfort of the covered open-air truck, tourists can enjoy a narrated tour of the historic Old Port area, see top landmark attractions like the Portland Observatory and the Victoria Mansion, and learn about Portland’s rich history.

The tour’s pickup and drop-off is right in the heart of the waterfront district on Commercial Street, so be sure to leave yourself plenty of time to find parking if you’re not walking from a downtown hotel–it’s nearly impossible to find street parking down by the water!

Address: 180 Commercial Street, Portland, Maine

16. Walk the Portland Freedom Trail

A tour of the Portland Freedom Trail gives visitors a better understanding of not only the local Underground Railroad and active abolitionists, but also that this port town’s trade activity once supported the triangular trade that kept slavery profitable.

This self-guided walking tour is easily done while exploring the Old Port and downtown Portland, with all of its landmarks located between Mountfort Street and Temple Street on the hill from Congress Street to the waterfront.

The Franklin Street Wharf (also known as the Maine State Pier, home of Casco Bay Lines) is its first stop and perhaps the most important to the active abolitionist movements. Not only was this port used by countless smaller boats and ships to carry escapees from Portland to safety in Canada, it was also the place many stowaways found help after journeys from the south on cargo ships. The shipyard was also a stable and good-paying source of work for those African Americans who could safely stay in the country.

Other top landmarks include meeting places critical to the anti-slavery movement, such as the Barber Shop of Jacob C. Dickson and the Abyssinian Church, and safehouses where runaways found refuge, like the home of Elias and Elizabeth Widgery Thomas.

The trail also features the homes of prominent African American activists like Charles Frederick Eastman and Alexander Stephenson, as well as other significant points of interest.

17. Go Kayaking in Casco Bay

Kayaking Casco Bay is one of Portland’s most popular things to do for active travelers, and is an equally popular activity with locals. The bay’s calm, protected waters make it a great place to learn, and give tourists the opportunity to explore the Calendar Islands at their own pace.

If you’re looking for a kayak rental, tour, or lesson that departs right from the city, Portland Paddle is an excellent option. It is located right by the East End Boat Launch, near Fort Allen Park on the Eastern Promenade Trail.

Nanuq Kayaks is another good option, located out on the wharf opposite the Casco Bay Lines Ferry port, just off Commercial Street. This shop focuses on kayak sales and rentals, and although they do not run regular guided tours, they are happy to give recommendations to customers who would like to explore the Casco Bay with an experienced guide.

18. See Stars at Southworth Planetarium

This modest planetarium is operated by the faculty and students at the University of Southern Maine and is located right on campus, in the Science Building near downtown. A visit to see the star show is an excellent thing to do on a rainy day in Portland.

The planetarium offers a good variety of shows, with both traditional stargazing presentations and topic-focused shows, including a fascinating show about the relationship between mythology and astronomy. There’s also the kid-favorite dinosaur show, a 360-degree trip to Mars, views from the Hubble Telescope, and other exciting presentations.

The Planetarium includes a modest exhibit area that displays examples of vintage telescopes and newer technology, and offers exhibits about the history of astronomical science.

Address: 70 Falmouth Street, Portland, Maine

19. Follow Bigfoot to the International Cryptozoology Museum

For a truly unique experience, anyone interested in the mysteries of unknown or unidentified animals needs to visit Portland’s International Cryptozoology Museum. Founded by cryptid devotee Loren Coleman, the museum contains an eclectic collection of items related to all manner of mysterious creatures, from Bigfoot to Yowie.

You might be surprised to find that the collection also includes some of the famous “fakes” like the Feejee Mermaid and jackelopes. The choice to include both disproven and unproven artifacts is intentional, acknowledging the fact that cryptozoologists must remain skeptical despite their enthusiasm.

The collections also include a great deal of pop-culture memorabilia, as the museum tries to explore the ways that cryptozoology influences culture, and vice-versa. While you’re here, be sure to take selfies with Bigfoot and the Creature from the Black Lagoon!

Address: 11 Avon Street, Portland, Maine

20. Enjoy the Local Art Scene

Thanks to a vibrant arts community supported by local universities and dozens of galleries, you don’t need to set foot in a museum to enjoy art in Portland. You will find truly artistic street-art murals throughout the city, from the alleys tucked away on side streets to beautiful public spaces like Congress Square Park.

On the first Friday of every month from 5 to 8pm, Portland’s First Friday Art Walk is a free self-guided tour of art galleries, museums, studios, and alternative art venues. Centered mainly in the Arts District, but with stops throughout the city, the Art Walk is a chance to sample Portland’s art scene, visit galleries and museums (the Portland Museum of Art is open free then), see live performances, and buy work directly from artists.

At any time, you’ll find plenty of art galleries to visit, whether you’re in the mood to buy or just to admire. Congress Street is home to the Congress Square Gallery, Maine Craft Portland, Bridge Gallery, and Bomb Diggity Arts, among others. Fore Street Gallery is nearby, and just up the street from them is Güven Gallery Anatolian Art, where you will find ancient designs incorporated into contemporary works.

If you are down by the water, Casco Bay Artisans on The Maine Wharf at 68 Commercial Street is home to works by over 50 artists. This is a multi-media gallery, offering everything from drawings and paintings to sculpture and textiles, with an overall Maine theme.

21. Go to the Theater

It is no surprise that Portland’s visual arts scene is complemented by an abundance of performing arts venues. The State Theatre is a top venue located downtown on Congress Street, hosting live musical and theatrical performances, as well as screenings of independent and foreign films. Its sister property, the Depot Pavilion at Thompson’s Point, is an outdoor venue that holds larger music events and concerts for all ages.

If you are in the mood for a more classic theater experience, check out the lineup offered by Portland Stage. They have multiple venues, including the 287-seat Mainstage Theater, the 75-seat black box Studio Theater, and the Susie Konkel Theater for Kids.

Merrill Auditorium hosts the Portland Symphony Orchestra, and the Portland Ballet offers multiple performances throughout the year.

22. Go Shopping on Congress Street

Portland is full of quirky shops and interesting finds, but you don’t even have to leave the main drag to get in a full day’s shopping at some of its most interesting stores. Electric Buddhas is our top pick, a nostalgiac’s dream that sells everything from vintage toys to 1980s video game systems. Attractively arranged, it’s almost like visiting a small museum where you can touch (most of) the displays.

Strange Maine is just up the hill, packed to the gills with an eclectic mix of toys, records, books, comics, and pretty much anything else you weren’t expecting. Moody Lords is another great spot for vinyls and vintage finds, and in the same building, you can find chic retro clothes at Vintage Vault.

Renys Department Store is another downtown shop you shouldn’t miss–this small chain is a Maine institution, and deserves a walk-through at the very least. It’s one of the very last old-school department stores, and you can find everything you need (and didn’t know you needed) for budget prices.

Across the street, Portland Flea-for-All is a funky upscale indoor flea market, but it’s only open Fridays and Saturdays for limited hours, so be sure to plan ahead.

23. Visit the Winslow Homer Studio at Prout’s Neck

The artist Winslow Homer painted many of his iconic images of the sea and the wave-splashed Maine coast from his studio overlooking the ocean on Prouts Neck, a point of land in nearby Scarborough. The studio has been restored, and is owned by the Portland Museum of Art; you can visit Homer’s studio on a tour conducted by the museum.

Inside the rustic studio are artifacts relating to Homer, as well as his easel, standing in front of the window just as it did when he painted there. You’ll see his paint box and some of the actual props he used in his paintings.

A newspaper rack holds reproduction pages of Harpers Weekly, with his illustrations of current events. Even though none of his paintings hang in the studio, you get a feel not only for the artist, but for the rocky coast he portrayed.

A cliff walk circles Prouts Neck, so you can see more of the ragged coast that inspired Homer.

24. Sample Local & International Cuisine

Capturing a full account of all the drool-worthy restaurants in Portland would take its own long list. This small city is big on food, and in addition to the expected plethora of seafood restaurants, it has an astounding variety of international restaurants that serve authentic cuisine.

If you’re downtown, head to Marcy’s Diner at the corner of Oak and Free Streets for a hearty breakfast in a retro setting before heading out for a day of sightseeing. For lunch, head to Congress Street for light Mexican fare at Taco Escobar, artisanal pizza at Otto, or meat-free selections at Green Elephant Vegetarian.

There are plenty of places to find great Asian food, and Yosaku on York Street is a top choice for sushi and other Japanese specialties. If you are looking for something truly unique, check out Asmara on Oak Street for authentic Eritrean and Ethiopian cuisine.

Commercial Street is where you will find the most seafood restaurants, like Gilberts Chowder House, which you can find right out on Custom House Wharf. Solo Italiano is right next door, or if you are looking for more varied Mediterranean dishes, head to nearby TIQA. Veranda Noodle House satisfies cravings for traditional Vietnamese noodle dishes, while Elevation Burger is the go-to for beef lovers.

While there are plenty of great desserts on offer at these restaurants and sweet shops around town, be sure to stop by Beal’s Ice Cream in the Old Port to satisfy that mid-afternoon sweet tooth.

25. Admire the Architecture

If you enjoy admiring or photographing interesting architecture, you will not be disappointed in Portland. In the Old Port and along Commercial Street, you will find a range of stone-and-brick buildings, many of which once served as warehouses and factories that were part of the thriving sea trade.

The United State Customs House, located across from Customs House Wharf, was completed in 1872 in the Renaissance Revival style and continues to house the government agency to this day.

The Tate House, a historic museum house located on Westbrook Street, is a perfect example of Colonial Style, dating back to 1755. The Victoria Mansion is an excellent example of Italianate architecture, while the Clapp House on Spring Street is in the Greek Revival style.

You will find lovely Art Deco buildings downtown, like the Time and Temperature Building and its ornate neighbor (now People’s Bank), which features a remarkably well-preserved stone-carved façade.

Map of Things to Do in Portland, ME

Portland, ME – Climate Chart