12 Fun Things to Do in Portland, Maine (My Favorite Attractions)

Portland, Maine, is a small city with a big personality—charming, walkable, and packed with coastal New England vibes. Imagine strolling along cobblestone streets in the Old Port, where historic brick buildings meet stunning harbor views. Or catching a sunset from the iconic Portland Head Light, a lighthouse straight out of a postcard. I’ve spent countless weekends exploring this coastal gem, and trust me, Portland has everything you need. Here are 12 things you don’t want to miss in this vibrant coastal city.

Best Things to See and Do in Portland, Maine

Visiting Portland, Maine? Stroll through the charming Old Port, tour the historic Portland Head Light, or explore the exhibits at the Portland Museum of Art. Take a scenic cruise around Casco Bay, savor fresh lobster at Eventide Oyster Co., or hike the trails at Presumpscot River Preserve. Whether you’re here for history, coastal views, or incredible seafood, Portland offers an unforgettable New England experience.

1. Old Port

The Old Port is where Portland’s history meets its lively waterfront energy. Walking through its cobblestone streets, you’ll be surrounded by 19th-century brick buildings, now home to boutique shops, cozy cafés, and vibrant bars. Commercial Street runs parallel to the harbor, offering fantastic seafood restaurants and stunning water views. One of my favorite stops here is Eventide Oyster Co., where the lobster roll is worth every bite. For a scenic stroll, head to the Portland Pier, where you can watch fishermen unload their daily catch or hop on a Casco Bay cruise.

Beyond the shops and restaurants, Old Port has a buzzing nightlife scene. Live music spills from bars like Port City Music Hall, and local breweries like Gritty McDuff’s serve up craft beers with a view. Whether you’re here for the food, the shopping, or just the atmosphere, Old Port is a must-visit.

2. Peaks Island

A short Casco Bay Lines ferry ride from downtown, Peaks Island is the perfect escape from the city’s bustle. As soon as you arrive, you’ll feel the island’s laid-back charm, with quiet roads, stunning ocean views, and a tight-knit community of artists and locals. Renting a golf cart or bike from Brad’s Bike Rental & Repair makes exploring easy. The island is small but packed with sights, from Battery Steele, a historic World War II fort, to hidden beaches with tide pools waiting to be explored.

Peaks Island is a haven for nature lovers. You can kayak along the rocky shoreline, relax on Centennial Beach, or browse quirky art galleries like Gem Gallery. For a perfect island day, grab ice cream from Peaks Café, watch the sunset over Casco Bay, and take the ferry back under the city lights.

3. Portland Museum of Art

Art lovers shouldn’t miss the Portland Museum of Art, home to over 22,000 works spanning centuries. Located in the Arts District, this museum showcases everything from classic European paintings by Monet and Renoir to modern pieces from Maine-based artists. One of my favorite stops here is the Winslow Homer collection, which captures the beauty of New England’s rugged coast. The museum also hosts rotating exhibitions, so there’s always something new to discover.

Beyond the galleries, the museum’s architecture is a work of art itself. Designed by I.M. Pei, the building blends historic charm with modern design. You can take a guided tour or explore at your own pace. After your visit, stroll down Congress Street to grab a coffee at Tandem Coffee Roasters or check out local shops. Whether you’re an art enthusiast or just looking for a quiet afternoon, this museum is a must-see.

4. Eastern Promenade

If you’re looking for the best oceanfront views in Portland, head to the Eastern Promenade. This 68-acre park stretches along Casco Bay, offering scenic walking trails, picnic spots, and access to East End Beach—one of the best places in the city for a summer swim. On my last visit, I took a morning walk along the Eastern Promenade Trail, a former railway line that winds through the park and connects to Fort Allen Park, which has incredible views of the harbor.

The Eastern Promenade is a year-round gem. In the summer, you’ll see people kayaking, paddleboarding, and biking along the trails. Fall brings crisp air and stunning foliage, while winter turns the park into a peaceful, snow-covered retreat. Whether you’re here for a morning jog, a lazy afternoon picnic, or just to soak in the coastal scenery, the Eastern Promenade is a must-visit in Portland.

5. International Cryptozoology Museum

If you’re fascinated by the unknown, the International Cryptozoology Museum is a must-visit in Portland’s Arts District. This quirky museum is dedicated to legendary creatures like Bigfoot, the Loch Ness Monster, and Mothman. Walking through the exhibits, you’ll find life-sized models, rare artifacts, and scientific theories about these mysterious beings. I was surprised by how much research goes into cryptozoology—some displays even present DNA evidence and documented sightings from around the world.

Beyond the famous cryptids, the museum showcases bizarre oddities, including a Fiji mermaid and preserved footprints of alleged unknown species. Whether you’re a believer or just curious, it’s an entertaining and educational stop. Kids love the hands-on exhibits, and adults enjoy the blend of folklore and science. If you’re looking for one of the most unique things to do in Portland, this museum offers an experience you won’t forget.

6. Portland Observatory

Standing tall on Munjoy Hill, the Portland Observatory is the last remaining maritime signal tower in the U.S. Since 1807, it has helped sailors navigate the busy harbor, and today, it offers some of the best panoramic views of Portland and Casco Bay. The guided tour takes you through the tower’s history, explaining how shipowners once used it to spot incoming vessels long before radios existed. I remember climbing its 103 steps—definitely a workout, but completely worth it!

At the top, you’ll get breathtaking views of the Old Port, Fort Gorges, and Peaks Island. You can even see Mount Washington on a clear day. The Observatory is only open seasonally, from late May to early October, so plan accordingly. If you love history and scenic lookouts, this is one of Portland’s top attractions that you shouldn’t miss.

7. Munjoy Hill

One of Portland’s most charming neighborhoods, Munjoy Hill blends history, food, and coastal beauty. Once a working-class district, it’s now a hotspot for trendy cafés, historic homes, and scenic waterfront views. Walking up Congress Street, you’ll find local favorites like Hilltop Coffee Shop and The Front Room, where brunch is always a great choice. The neighborhood’s relaxed vibe makes it the perfect place to wander, whether you’re exploring Eastern Promenade or admiring Victorian-era architecture.

Munjoy Hill is also home to Fort Allen Park, a peaceful green space with sweeping views of Casco Bay. On warm days, locals gather here for picnics, yoga, and sunset watching. If you’re a fan of history, stop by the Portland Observatory for a glimpse into the city’s maritime past. Whether you’re here for food, nature, or the views, Munjoy Hill has something special to offer.

8. The Maine Narrow Gauge Railroad Co. & Museum

If you love history or trains, the Maine Narrow Gauge Railroad Co. & Museum is a fantastic way to step back in time. Located near Munjoy Hill, this museum preserves Maine’s unique two-foot gauge railroads, which were once used to transport goods and passengers across the state. The highlight? A scenic train ride along the Eastern Promenade, offering fantastic views of Casco Bay as you ride in vintage railcars.

Inside the museum, you’ll find historic locomotives, hands-on exhibits, and fascinating stories about Maine’s railroad history. Kids love the model train displays, and train enthusiasts will appreciate the well-preserved artifacts. The museum runs special themed rides throughout the year, including holiday trains and pumpkin patch rides, making it a fun stop for families. Whether you’re a history buff or just looking for a unique experience, this is one of Portland’s hidden gems.

9. Arts District

Portland’s Arts District is a cultural hotspot packed with galleries, theaters, and museums that showcase Maine’s thriving creative scene. Stretching along Congress Street, this area is home to the Portland Museum of Art, which houses works by Claude Monet, Winslow Homer, and local Maine artists. Walking through the district, you’ll also find smaller galleries like Greenhut Galleries and SPACE, where contemporary artists push creative boundaries.

Beyond visual arts, the district features live performances at Merrill Auditorium and Portland Stage Company. I once stumbled into a street performance near Monument Square—unexpected moments like that make this area so lively. If you’re here on the First Friday Art Walk, the streets come alive with music, open studios, and food vendors. Whether you love fine art, theater, or live music, Portland’s Arts District is a must-visit for culture lovers.

10. Victoria Mansion

Stepping inside Victoria Mansion feels like traveling back to the 1850s Gilded Age. This Italianate-style mansion, located on Danforth Street, is one of the most well-preserved historic homes in the country. Originally built for a wealthy hotelier, the mansion boasts intricate hand-painted ceilings, carved woodwork, and luxurious furnishings—about 90% of the interior remains original. The guided tours dive into Portland’s wealthy past and the lives of the people who lived here, offering a fascinating glimpse into 19th-century high society.

The mansion is open seasonally from May to October, and during Christmas, it transforms into a dazzling holiday display with festive decorations. I visited in December, and seeing the Victorian-style holiday décor was a highlight of my trip. Whether you’re into architecture, history, or interior design, Victoria Mansion offers a unique and immersive experience of Portland’s 19th-century elegance.

11. Palace Playland

Located in Old Orchard Beach, Palace Playland is New England’s only beachfront amusement park, making it one of the most fun attractions near Portland, Maine. This seasonal park is packed with classic carnival rides, from the spinning Tilt-A-Whirl to the towering Galaxi Coaster. The Ferris wheel, offering stunning ocean views, is a must-try, especially at sunset. If you enjoy arcade games, the park boasts one of Maine’s largest indoor arcades, filled with everything from skeeball and racing games to modern video games.

Palace Playland is a family-friendly destination, but thrill-seekers will love the park’s high-speed rides and bumper cars. After a fun-filled day, you can grab fresh seafood or classic boardwalk treats at one of the many nearby restaurants. Whether you’re visiting with kids, friends, or your inner child, Palace Playland delivers an unforgettable mix of nostalgia and excitement.

12. Rockin’ Horse Stables

For a charming countryside experience, head to Rockin’ Horse Stables in Kennebunkport, just a short drive from Portland, Maine. This family-run stable offers horse-drawn carriage and sleigh rides, making it a perfect year-round activity. In winter, sleigh rides through snow-covered trails feel like stepping into a holiday postcard. The crisp air, jingling bells, and cozy blankets create a magical atmosphere, while complimentary hot chocolate warms you up after the ride.

During warmer months, the carriage rides offer a scenic tour through Maine’s picturesque countryside, making it a great addition to any romantic getaway or family trip. Whether you’re looking for a unique date idea, a relaxing ride, or a fun family adventure, Rockin’ Horse Stables delivers a truly memorable experience. It’s an authentic and peaceful way to explore Maine’s natural beauty in every season.

Frequently Asked Questions (FAQs) about the Best Things to Do in Portland, Maine

Looking for more content on the top things to do in Portland, Maine? Here are some popular questions (and answers) I get that will help you plan your trip to Portland:

When is the best time to visit Portland, Maine?

Portland, Maine, is a year-round destination, but the best time to visit depends on what you want to do. For outdoor activities and festivals, summer and fall are the best seasons. Winter, on the other hand, offers unique experiences like ice skating and winter festivals.

Is Portland Maine worth visiting?

Yes, Portland, Maine, is indeed worth visiting, and it has much to offer to travelers. As the largest city in Maine, Portland is known for its vibrant arts scene, historic architecture, and stunning waterfront.

The Old Port district is a must-see, with its cobblestone streets, 19th-century brick buildings, and an array of boutiques, galleries, and restaurants. Here, you can enjoy some of the freshest seafood, including the famous Maine lobster. The city’s culinary scene is renowned, offering everything from gourmet dining to food trucks, all showcasing local ingredients.

Portland’s proximity to the sea means there are plenty of opportunities for sailing, fishing, and enjoying the beautiful coastal views. The city is also home to several lighthouses. This includes the iconic Portland Head Light, which is a popular spot for photography.

For art enthusiasts, the Portland Museum of Art houses an impressive collection of American, European, and contemporary art. Outdoor lovers will appreciate the nearby parks and trails, such as the Eastern Promenade, offering scenic views of Casco Bay.

With its blend of cultural attractions, natural beauty, and culinary delights, Portland, Maine, provides a unique and enjoyable experience for various interests and tastes. Whether you’re a foodie, history buff, or nature lover, Portland has something special to offer.

What are the must-see attractions in Portland, Maine?

Portland, Maine, is known for its vibrant arts scene, historic lighthouses, and beautiful parks. Some must-see attractions include the Portland Head Light, the Old Port district, and the Eastern Promenade. For art lovers, the Portland Museum of Art is a must-visit.

What are the best outdoor activities in Portland, Maine?

Portland offers a wide range of outdoor activities. You can enjoy hiking and biking in the city’s parks, go sailing or fishing in Casco Bay, or take a scenic drive along the Maine coast. In winter, you can enjoy ice skating or cross-country skiing.

Is Portland, Maine a good tourist destination?

Absolutely! Portland, Maine is a fantastic tourist destination. It’s a city that effortlessly blends rustic New England charm with a vibrant arts scene and a foodie culture that’s recognized nationwide. Exploring the historic Old Port district, visiting the iconic lighthouses, or indulging in some of the freshest seafood? Portland offers a unique and memorable experience for all types of travelers.

What is Portland, Maine’s #1 attraction?

While it’s hard to pick just one, many would argue that the Portland Head Light is the number one attraction in Portland, Maine. This historic lighthouse, located in the stunning Fort Williams Park, is the oldest in Maine and offers breathtaking views of the rugged coastline. It’s a must-visit for any first-time visitor to Portland and a beloved symbol of the city’s maritime heritage.

Is there a lot to do in Portland?

Yes, there’s a lot to do in Portland, Maine, catering to a wide range of interests and preferences.

1. Culinary Exploration: Portland’s food scene is renowned, and you can enjoy everything from gourmet meals to casual food trucks. Don’t miss the chance to try fresh seafood, especially the famous Maine lobster.
2. Historic Sites: The Old Port district offers a glimpse into Portland’s history with its cobblestone streets and 19th-century architecture. Guided tours are available to learn more about the area’s rich past.
3. Art and Culture: The Portland Museum of Art and other galleries showcase a variety of art collections. The city also hosts various cultural festivals and events throughout the year.
4. Outdoor Activities: Enjoy the natural beauty of the area by visiting the Eastern Promenade or taking a ferry to the nearby Casco Bay Islands. Opportunities for hiking, biking, sailing, and fishing abound.
5. Lighthouses: Portland is home to several iconic lighthouses, including Portland Head Light, offering great photo opportunities and beautiful coastal views.
6. Shopping: From unique boutiques in the Old Port to larger shopping centers, Portland offers a variety of shopping experiences.
7. Breweries: Portland has a thriving craft beer scene. Many breweries offer tours and tastings, making it a great destination for beer enthusiasts.
8. Music and Nightlife: The city has a lively music scene with venues hosting live performances. They range from local bands to nationally recognized acts. There are also plenty of bars and clubs for those looking to enjoy the nightlife.
9. Seasonal Activities: Depending on the time of year, you can enjoy seasonal activities like skiing or snowboarding in the winter. Or, you can take advantage of beach outings and outdoor festivals in the summer.

With its diverse offerings, Portland, Maine, ensures that visitors of all ages and interests can find enjoyable activities and attractions.

Final Thoughts on Exploring Portland, Maine

From its historic lighthouses to its vibrant arts scene, Portland, Maine, offers a unique blend of natural beauty and cultural richness. You’ll find plenty to see and do in this charming New England city. So why wait? Start planning your Portland adventure today and discover the unique places in Portland, Maine, that make it a must-visit destination on any New England itinerary.

For more travel inspiration, check out our other articles on New England destinations. For a weekend getaway or a longer vacation, we’ve got you covered with the best places to visit, things to do, and hidden gems to discover. Happy travels!