23 Best & Fun Things To Do in Portland (Maine)

Portland, Maine, is the largest city in Maine, with around 68,000 residents. It is also known as “The Forest City.” Portland sits on a scenic peninsula in Casco Bay on the Atlantic Ocean. It has a vibrant port that once made it a major shipping and trading center. Today, it stands as New England’s second-largest seaport by tonnage.

The city’s geography is a mix of coastal charm and urban character. Its neighborhoods are diverse, from the historic Old Port with cobblestone streets and 19th-century architecture to the Arts District, home to galleries, theaters, and the Portland Museum of Art.

The Eastern Promenade provides stunning ocean views, while Deering Oaks Park offers a green retreat. Portland is known for its creative economy, strong arts scene, and culinary reputation.

Its restaurants and breweries have gained national attention, and the food culture draws locals and visitors alike. The city also holds a historical link to its English namesake, Isle of Portland, and its notable resilience, represented by a phoenix on its city seal.

Are you wondering what to do in Portland? Check out the best things to do in Portland, Maine.

Things To Do in Portland, Maine

1. Visit the Old Port District

The Old Port District in Portland, Maine, is a historic area full of charm. Walk down cobblestone streets lined with 19th-century brick buildings. Here, you’ll find unique boutiques, art galleries, and specialty shops, perfect for browsing or picking up a local souvenir.

The area is famous for its seafood restaurants and breweries, offering fresh Maine lobster and a vibrant craft beer scene. Try places like J’s Oyster or the Old Port Sea Grill for a taste of the local catch.

This district is also known for its lively atmosphere, especially during summer when the harbor is bustling with boats. The smell of fresh ocean air mixed with delicious food aromas fills the area. From trendy cafes to cozy pubs, there’s something for everyone.

The Old Port isn’t just about food and shopping; it also offers a glimpse into Portland’s maritime heritage. Look out for historical plaques and landmarks along your walk. If you’re visiting in June, don’t miss the Old Port Festival, an annual celebration of music, art, and food.

Address: Old Port District, Portland, ME 04101

2. Explore the Portland Head Light

Portland Head Light is one of Maine’s most iconic landmarks. This lighthouse has guided sailors since 1791. Today, it’s a popular spot for photography, with breathtaking ocean views. Its striking white tower against the rugged Maine coastline makes it a must-see. The lighthouse sits on a rocky cliff, providing dramatic scenes as waves crash below.

Visitors can explore the museum inside the former lighthouse keeper’s house, which offers insights into the lighthouse’s history and Maine’s maritime legacy. Outside, walking trails wind through Fort Williams Park, leading to various lookout points and a small beach.

Picnic tables dot the area, so pack a lunch and enjoy the view. Kids and adults alike will enjoy spotting boats and watching the seabirds that frequent the area. Portland Head Light is perfect for anyone looking to experience Maine’s coastal beauty.

Address: 1000 Shore Rd, Cape Elizabeth, ME 04107

3. Stroll the Eastern Promenade

The Eastern Promenade offers a scenic, 2.1-mile trail that follows the coast of Casco Bay. This green space is ideal for walking, jogging, or just relaxing with a beautiful waterfront view. It’s especially popular during sunrise and sunset, when the light casts a stunning glow over the water. On a clear day, you can even spot several islands in the bay.

The promenade features picnic areas, benches, and a playground, making it perfect for families or anyone looking for a leisurely outing. Along the way, you’ll find plenty of spots to stop and take in the sights, like the historic Fort Allen Park.

The area was built in 1891. It provides a glimpse into Portland’s past with its old cannons and informational signs. The Eastern Promenade also has a sandy beach area, where you can dip your toes in the cool Atlantic waters or enjoy a peaceful moment by the shore.

Address: Eastern Promenade Trail, Portland, ME 04101

4. Check out the Portland Museum of Art

The Portland Museum of Art is the largest and oldest public art institution in Maine. It boasts a collection of over 18,000 works, including pieces by renowned artists like Winslow Homer, Claude Monet, and Andrew Wyeth. Art lovers will enjoy the museum’s mix of European and American masterpieces, modern art, and contemporary pieces.

The museum also hosts rotating exhibitions, so there’s always something new to see. Inside, the museum’s layout is spacious and inviting. One standout area is the McLellan House, a historical mansion that’s part of the museum and offers insight into 19th-century Portland life.

Don’t miss the rooftop sculpture garden, which has a lovely view of the city. The museum frequently offers guided tours, workshops, and family-friendly activities, making it a welcoming space for all ages. 

Address: 7 Congress Square, Portland, ME 04101

5. Discover Marine Life at the Gulf of Maine Research Institute’s Cohen Center

The Gulf of Maine Research Institute’s Cohen Center offers a unique experience focused on Maine’s marine environment and ecosystem. It’s a top choice for those interested in the ocean and its impact on Maine’s communities. Through hands-on exhibits and interactive learning, the center explores everything from the fishing industry to climate change’s effects on marine life.

The Cohen Center’s “LabVenture” program lets visitors, especially families and school groups, get hands-on with marine science. They can explore a digital aquarium, analyze real-time data, and even simulate the work of marine biologists.

The center’s focus on science education makes it a dynamic learning environment for both kids and adults. Plus, it’s free to the public, making it accessible to everyone. The exhibits are designed to be engaging and informative, offering a fresh perspective on Maine’s coastal ecosystem.

Address: 350 Commercial St, Portland, ME 04101

6. Walk Through Deering Oaks Park

Deering Oaks Park is a beautiful, historic green space right in Portland. It covers 55 acres and offers plenty of activities and sights, making it a favorite local spot for relaxation and outdoor fun. The park has a lovely duck pond where visitors can watch the ducks and even feed them. Nearby, there’s a splash pad open in the summer, which is a hit with kids and families.

On Saturdays, the park transforms into a bustling hub with the Portland Farmers’ Market, where you can buy fresh, local produce, artisan goods, and flowers. Deering Oaks is also known for its large oak trees, which provide ample shade, making it an ideal spot for picnics or reading a book.

Walking trails wind through the park, connecting various areas like the tennis courts, playground, and rose garden. In winter, the duck pond turns into an ice skating rink, creating a charming seasonal experience.

Address: 33 Deering Ave, Portland, ME 04101

7. Visit the Historic Wadsworth-Longfellow House

The Wadsworth-Longfellow House is a historic gem and the childhood home of renowned poet Henry Wadsworth Longfellow. It was built in 1785 and, as such, is the oldest standing structure on the Portland peninsula.

The house offers a fascinating glimpse into 18th- and 19th-century life in Maine. It has been preserved with authentic furnishings, decor, and family artifacts, giving visitors a unique view of the poet’s early surroundings.

Tours of the Wadsworth-Longfellow House are both informative and engaging, led by knowledgeable guides who share stories about the Wadsworth and Longfellow families. Visitors can explore the family’s personal rooms, including Henry’s study and the formal dining room.

The adjoining Longfellow Garden, a peaceful oasis with blooming flowers and shaded paths, adds an extra touch of charm. This site is a must for history buffs and literature lovers, as it connects Maine’s history with one of America’s most beloved literary figures.

Address: 489 Congress St, Portland, ME 04101

8. Enjoy the Collections at the Victoria Mansion

Victoria Mansion is a beautifully preserved example of pre-Civil War architecture and design. This historic home, built in 1860, reflects the grandeur and elegance of the Victorian era. Known for its ornate interiors, the mansion features elaborate woodwork, original stained glass, and intricate frescoes on the ceilings and walls. Every room has been meticulously restored, showcasing opulent 19th-century furnishings.

Visitors will appreciate the mansion’s impressive collections, which include lavish furniture, artwork, and textiles. Guided tours are available, providing a rich narrative of the house’s history and its original owners, the Morse family.

Each room reveals a story about Victorian society, highlighting the contrasts between public grandeur and private life. The mansion is especially captivating during the holidays when it’s decorated in seasonal splendor. Victoria Mansion offers a rare chance to step back into a time of elegance and extravagance, making it an essential Portland experience.

Address: 109 Danforth St, Portland, ME 04101

9. Take a Ferry Ride to Peaks Island

A short ferry ride from Portland takes you to Peaks Island, a small, charming island in Casco Bay. It is known for its laid-back vibe and natural beauty. making it perfect for a relaxing day trip. The ferry ride itself is a delight, offering views of the bay and Portland’s waterfront. Once on the island, visitors can rent bikes, stroll along the beaches, or simply enjoy the slower pace of island life.

On Peaks Island, you’ll find a mix of cozy cafes, art galleries, and local shops, making it easy to explore and discover local craftsmanship. The island is also home to the Umbrella Cover Museum, a quirky attraction dedicated to umbrella covers from around the world.

For those interested in history, the World War II-era Battery Steele is open to explore, with its tunnels and bunkers adding an adventurous twist. Whether you’re looking for a beach day or a bike ride, Peaks Island is an ideal escape.

Address: Casco Bay Lines Ferry Terminal, 56 Commercial St, Portland, ME 04101

10. Browse the Art Galleries and Exhibitions in Portland’s Arts District

Portland’s Arts District is a vibrant neighborhood that’s a must-visit for art lovers. Located along Congress Street, the district is packed with galleries, studios, and unique exhibits. From contemporary paintings to traditional crafts, the area offers an eclectic mix of art forms that appeal to all tastes.

Major stops include the Portland Museum of Art, where you’ll find works by renowned artists like Winslow Homer and Edward Hopper, and SPACE Gallery, which showcases cutting-edge contemporary art and performance.

Every month, the district hosts a First Friday Art Walk, a lively evening when galleries open their doors to the public, often with live music and local food vendors. It’s a great way to meet artists and get a feel for Portland’s creative scene.

Small, independent galleries also dot the area, each with its own unique atmosphere and displays. For anyone interested in experiencing Portland’s cultural heart, the Arts District is the place to be.

Address: Congress St, Portland, ME 04101

11. Learn About Local History at the Maine Historical Society and Museum

The Maine Historical Society and Museum is a fantastic spot to dive into Maine’s rich history. The museum is located next to the Wadsworth-Longfellow House. It offers engaging exhibits that cover topics from Maine’s Indigenous history to its maritime heritage.

Through artifacts, photographs, and interactive displays, visitors can explore Maine’s development over the centuries and understand its role in shaping New England. One highlight of the museum is its Research Library, which houses an extensive collection of historic documents and records. It’s a valuable resource for anyone tracing family history or interested in Maine’s past.

Another fascinating exhibit is the “Becoming Maine” gallery, which covers Maine’s journey to statehood and its historical milestones. The Maine Historical Society frequently hosts lectures, workshops, and special events, making it a dynamic place to learn and explore. It’s an ideal stop for history enthusiasts and curious travelers alike.

Address: 489 Congress St, Portland, ME 04101

12. Catch a Show or Concert at the State Theatre, an Iconic Music Venue

The State Theatre is one of Portland’s most iconic music venues, attracting a mix of local talent and big-name artists. This historic theater, originally opened in 1929, combines stunning architecture with modern sound, creating an unforgettable concert experience. The venue has undergone careful restoration, preserving its original Art Deco details while adding top-notch acoustics and comfortable seating.

With a capacity of around 1,800, the State Theatre offers an intimate setting that makes every show feel personal. It’s hosted a diverse lineup of musicians, from indie bands and jazz ensembles to rock legends.

There’s something magical about catching a live show in this beautiful theater, with its plush velvet seats and ornate decor. The theater also has a great downtown location, making it easy to enjoy a night out with nearby restaurants and bars. 

Address: 609 Congress St, Portland, ME 04101

13. Tour the Allagash Brewing Company

Allagash Brewing Company is a must-visit for beer lovers in Portland. Allagash, which is known for its Belgian-style brews, has gained a nationwide reputation for quality and innovation.

When you tour the brewery, you’ll get an inside look at the brewing process, from selecting ingredients to bottling. The highlight is the tasting room, where you can sample a variety of their craft beers, including popular choices like Allagash White, their flagship wheat beer, and limited-edition seasonal brews.

The tour is not just about beer but also about sustainability, as Allagash places a strong focus on eco-friendly practices. Knowledgeable guides make the experience engaging, explaining the craft and care behind each brew. There’s also a cozy outdoor area where visitors can relax with their beer and enjoy the laid-back Portland vibe. 

Address: 50 Industrial Way, Portland, ME 04103

14. Relax at Fort Allen Park

Fort Allen Park on the Eastern Promenade is a beautiful spot to unwind while taking in panoramic views of Casco Bay. It was originally built as a military fort in 1775. Today, it’s a peaceful green space where visitors can picnic, stroll, or simply sit back and enjoy the ocean breeze. The park has several historical monuments, including cannons from the Civil War era and a memorial for the USS Maine.

The scenic location is perfect for watching the sunrise or catching a glimpse of the islands in Casco Bay. Benches and picnic tables are scattered throughout, making it a comfortable place for a picnic.

In warmer months, the park hosts concerts and local events, adding to its lively charm. Fort Allen Park is also popular with dog walkers, joggers, and families looking for a relaxing outdoor escape. It’s a must-see for anyone wanting to experience Portland’s natural beauty.

Address: Eastern Promenade, Portland, ME 04101

15. Explore the Unique Shops at the Public Market House

The Public Market House in downtown Portland is a cozy, two-story marketplace filled with unique shops and food stalls. It’s a great spot to grab a bite or find a one-of-a-kind souvenir. Local vendors sell everything from artisanal cheeses and baked goods to handcrafted jewelry and Maine-made gifts. For food lovers, the Market House offers plenty of choices, including fresh coffee, smoothies, and comfort foods.

The atmosphere is relaxed and friendly, with a community feel that’s inviting to both locals and visitors. Upstairs, there’s a seating area with views of Monument Square, perfect for people-watching while you enjoy your meal.

The Public Market House is ideal for a quick stop or a leisurely browse, and it’s especially popular during the colder months when indoor markets become cozy retreats. If you want to taste local flavors or find a special gift, this market is a Portland highlight.

Address: 28 Monument Square, Portland, ME 04101

16. See Wildlife and Wetlands on a Walk Through the Fore River Sanctuary

The Fore River Sanctuary is a hidden gem in Portland, perfect for nature lovers and birdwatchers. This 85-acre preserve offers peaceful trails winding through wetlands, forests, and meadows. The sanctuary’s main trail leads you to Jewell Falls, Portland’s only natural waterfall, where you can relax and listen to the gentle rush of water. As you walk, you’ll likely spot various wildlife, including birds, turtles, and even deer.

The trails are easy to navigate and are suitable for all ages. In spring and summer, the sanctuary bursts with wildflowers and greenery, while autumn brings vibrant foliage. The wetland areas are home to unique plant species and provide crucial habitats for migrating birds, making it a top spot for birdwatching.

The Fore River Sanctuary is managed by Portland Trails, a nonprofit dedicated to maintaining local green spaces. It’s a peaceful retreat from city life and a must-visit for anyone seeking a quiet escape into nature.

Address: Rowe Ave, Portland, ME 04102

17. Go for a Walk on the Western Promenade

The Western Promenade offers stunning views of the White Mountains and the Fore River, providing a scenic place to walk, relax, or have a picnic. This historic public park, designed in the late 1800s, is a favorite among locals and visitors for its beautiful landscapes and sweeping vistas. Lined with elegant Victorian-era homes, the promenade has a charming, old-world feel that adds to its appeal.

The Western Promenade has several benches along its path, making it easy to stop and enjoy the view. It’s also a popular spot for sunset watching, as the evening light casts a warm glow over the city.

During the winter, the area is peaceful and quiet, while warmer months bring locals enjoying outdoor activities. The promenade is well-maintained, with pathways perfect for a leisurely stroll. It’s a relaxing place to take in Portland’s natural beauty and a wonderful spot for photography.

Address: Western Promenade, Portland, ME 04102

18. Visit the International Cryptozoology Museum

The International Cryptozoology Museum is a quirky and fascinating attraction that dives into the world of mysterious creatures. Founded by cryptozoologist Loren Coleman, the museum houses an array of exhibits dedicated to legendary animals like Bigfoot, the Loch Ness Monster, and more. You’ll find everything from hair samples to life-sized models, as well as historical artifacts connected to cryptozoology.

Visitors can explore displays on rare animal sightings and learn about the science behind cryptozoology. Each exhibit is filled with fun facts and intriguing details, making it a favorite among curious minds.

The museum also includes exhibits on well-known creatures in pop culture, blending science with folklore. This unique museum offers something different from typical attractions and is great for families or anyone with an adventurous spirit. 

Address: 4 Thompson’s Point Rd #106, Portland, ME 04102

19. Take a Sunset Cruise in Casco Bay

A sunset cruise in Casco Bay offers one of the most enchanting experiences in Portland. As the sun dips below the horizon, you’ll see the bay illuminated in hues of pink, orange, and gold. Casco Bay Lines and other local companies offer evening cruises that take you past scenic islands, historic forts, and iconic lighthouses.

It’s a perfect way to unwind and soak in Maine’s coastal beauty. The cruises often include live narration, sharing stories about Portland’s maritime history and unique landmarks.

You’ll have plenty of photo opportunities as seabirds and even harbor seals make occasional appearances. Most cruises offer indoor and outdoor seating, allowing you to enjoy the view from any spot. 

Address: 56 Commercial St, Portland, ME 04101 (Casco Bay Lines Terminal)

20. Enjoy Fresh Seafood at Becky’s Diner

Becky’s Diner is a Portland staple and one of the best spots to enjoy fresh seafood. This cozy, no-frills diner has been serving locals and visitors alike since 1991. It’s renowned for its hearty portions and authentic Maine dishes. Located on the waterfront, Becky’s has a relaxed, friendly vibe, and you’ll often find fishermen and locals sharing stories over breakfast.

The menu is packed with delicious options, including clam chowder, lobster rolls, and their famous fish sandwich. Breakfast is also a big hit here, with the blueberry pancakes being a favorite among regulars.

Becky’s is open early, making it a great spot for a hearty start to your day, but it’s also open for lunch and dinner. It’s a must-visit for anyone wanting to experience Maine’s seafood without the fuss, offering great food and warm service.

Address: 390 Commercial St, Portland, ME 04101

21. Experience the Children’s Museum & Theatre of Maine

The Children’s Museum & Theatre of Maine offers a fun and educational experience for families visiting Portland. Located in a new, state-of-the-art building, the museum is packed with interactive exhibits designed to engage children’s curiosity and creativity. Kids can explore hands-on activities in areas like the science lab, art studio, and even a mock fire station.

The museum also has an immersive theatre where children’s plays bring popular stories to life. It’s a fantastic opportunity for kids to enjoy live performances in an intimate setting.

The rooftop garden, with views of the city and harbor, is a highlight and a peaceful spot for families to take a break. The museum regularly updates its exhibits, ensuring that there’s always something new to discover. It’s an ideal destination for a day of learning, play, and family bonding.

Address: 250 Thompson’s Point Rd, Portland, ME 04102

22. Tour the Historic Portland Observatory

The Portland Observatory, built in 1807, is a must-see for history lovers and those curious about Maine’s maritime past. It’s the only remaining maritime signal tower in the United States. This seven-story wooden structure served as a communication tower, allowing ship owners to identify incoming vessels well before they reached the harbor. It’s an essential piece of Portland’s maritime heritage and offers a unique glimpse into the past.

Guided tours are available, giving visitors a detailed look at the observatory’s history and construction. As you climb to the top, you’ll see displays about Portland’s shipping history and learn how the signal flags once connected ship captains to the shore.

The highlight, of course, is the panoramic view from the top floor. From here, you can take in sweeping views of Portland’s skyline, Casco Bay, and the surrounding islands. It’s a beautiful sight and a rare experience to stand where ship watchers once did.

Address: 138 Congress St, Portland, ME 04101

23. Walk or Bike the Back Cove Trail

The Back Cove Trail is a scenic, 3.5-mile loop around Portland’s Back Cove, offering a great spot for a walk, run, or bike ride. The trail is mostly flat and well-maintained, making it accessible for all ages and fitness levels.

As you go around the cove, you’ll enjoy fantastic views of Portland’s skyline and the tranquil waters of the bay. It’s especially popular during sunrise and sunset, when the light reflects beautifully on the water.

Along the way, you’ll find benches and picnic spots, perfect for a quick rest or snack break. The trail is lined with trees and offers plenty of shade in the warmer months. It’s a favorite spot for locals to exercise, walk their dogs, or simply unwind outdoors.

The Back Cove Trail is also part of Portland’s larger network of trails, so you can easily extend your walk or bike ride into other parts of the city. It’s a relaxing way to experience Portland’s natural beauty.

Address: Back Cove Trail, Portland, ME 04101

Final Thoughts

Portland, Maine, offers a distinct blend of coastal charm, history, and vibrant local culture. This city’s friendly, laid-back vibe invites you to explore at your own pace.

One of the best tips for visiting is to embrace the walkability; many of Portland’s gems are best experienced on foot. Pack comfortable shoes and be prepared for changing weather, as coastal Maine can be unpredictable.

Locals are welcoming and knowledgeable, so don’t hesitate to ask for recommendations on dining, art, and hidden spots. And if you’re visiting in peak summer, plan and book accommodations early to secure your ideal stay.