Things to Do in Portland, Maine – A Local’s Guide to Top Attractions
Portland, Maine, is a beautiful coastal city filled with history, charm, and amazing food. With its cobblestone streets, scenic waterfront, and iconic lighthouses, it’s a place that feels both welcoming and exciting.
Whether you’re here for fresh seafood, craft breweries, or stunning ocean views, there’s always something to explore. You can stroll through the Old Port’s historic streets, take a ferry to the Casco Bay Islands, or simply relax by the harbor and watch the boats go by. No matter what kind of traveler you are, Portland is a city that’s easy to love and hard to forget!
Best Time to Visit
Portland, Maine is a great destination year-round, with each season offering something special. If you love outdoor activities, summer and early fall are perfect, while winter is great for a cozy, quieter getaway with indoor experiences.
For the best mix of pleasant weather and fewer crowds, consider visiting in April-May or September-October. These months offer mild temperatures, colorful scenery, and a more relaxed atmosphere as compared to the busy summer season. No matter when you visit, Portland has plenty to enjoy!
Things to do in Portland, Maine
1. Explore the Old Port District
The Old Port District is the heart of Portland, Maine. It is known for its cobblestone streets, historic brick buildings, and lively waterfront. This charming area is packed with boutique shops, art galleries, seafood restaurants, and craft breweries.
Stroll along the wharves, watch the fishing boats come in, or grab a famous lobster roll at a local eatery. Whether you’re shopping, dining, or just soaking in the coastal charm, the Old Port is a must-visit spot in Portland!
2. Enjoy Fresh Seafood & Local Cuisine
Portland is a food lover’s paradise, especially when it comes to fresh seafood. From famous lobster rolls to freshly shucked oysters, the city is home to some of the best seafood in New England.
Be sure to check out Eventide Oyster Co. for their signature brown butter lobster roll, or visit Portland Lobster Company for a classic waterfront dining experience. Beyond seafood, the city also boasts farm-to-table restaurants, cozy cafes, and award-winning bakeries. This makes it a must-visit destination for foodies!
3. Visit Portland Head Light & Fort Williams Park
No trip to Portland is complete without visiting the Portland Head Light, Maine’s oldest and most iconic lighthouse. It was built in 1791. Perched on the rocky shores of Cape Elizabeth. It offers breathtaking ocean views which makes it a dream spot for photographers and nature lovers alike.
It is located within Fort Williams Park. You can also explore scenic walking trails, historic ruins, and picnic areas. Grab a bite from one of the local food trucks, like the famous Bite Into Maine which serves up delicious lobster rolls with a view. Whether you’re taking in the coastal beauty, learning about maritime history, or simply enjoying the peaceful surroundings, this is a must-visit destination in Portland!
4. Take a Ferry to the Casco Bay Islands
Escape the hustle and bustle of Portland with a ferry ride to the Casco Bay Islands, where you can enjoy peaceful natural landscapes, charming communities, and outdoor activities. The ferry is a quick and easy way to explore these nearby islands, each with its own unique vibe.
Peaks Island: It is known for its relaxed atmosphere. Peaks Island is the most popular of the Casco Bay Islands. It’s perfect for cycling around, as the island offers a scenic loop road and plenty of beaches and parks to explore. You can rent bikes or kayaks, walk the ferry road, or enjoy a peaceful afternoon at Battery Steele, an abandoned WWII fort. The island also features local cafes, art galleries, and a small museum which showcases its rich history.
Great Diamond Island: A quieter option, Great Diamond Island is less touristy but equally stunning. It’s known for its serene walking trails, which lead you through forests and along the shoreline. The island is home to a small community with beautiful historic homes and sites like the Diamond Cove Resort. It is perfect for those seeking peaceful hikes, wildlife watching, and photography.
Chebeague Island: It is the largest island in the Casco Bay area. Chebeague is a perfect spot for those looking for both adventure and relaxation. It’s a popular destination for boating, kayaking, and fishing, and its sandy beaches that offer plenty of space for picnics and swimming.
It also boasts a golf course and local restaurants, where you can enjoy fresh seafood with a view of the water. The small-town charm of the island makes it an ideal place to unwind and enjoy the slower pace of island life.
Each of these islands offers a unique experience which makes them perfect for a day trip or a longer stay.
5. Discover Art & Culture
Portland is home to a thriving art and culture scene, with a variety of museums, historical sites, and galleries to explore.
- Portland Museum of Art: It is one of the most renowned cultural institutions of Maine. The Portland Museum of Art (PMA) boasts an impressive collection of American, European, and contemporary art. From works by Edward Hopper and Winslow Homer to rotating exhibits of modern artists, there’s something for every art lover here. Don’t forget to check out their beautiful sculpture garden and library which offers peaceful spots to enjoy the art.
- The Wadsworth-Longfellow House: Steep back in time and visit the Wadsworth-Longfellow House, the childhood home of famous poet Henry Wadsworth Longfellow. This National Historic Landmark offers a glimpse into the history of Portland and the life of one of America’s greatest poets. Explore the preserved rooms, historical exhibits, and lush gardens surrounding the home.
- Street Art & Galleries: Portland is known for its vibrant street art and local galleries. Wander through the city’s Arts District, where you’ll find murals, sculptures, and installations that reflect the creative spirit of the city. The Congress Street Gallery district is home to many local galleries that feature everything from contemporary art to classic works. Keep your eyes open for unexpected art popping up in alleys and public spaces which showcases Portland’s strong community of artists.
6. Outdoor Adventures
Portland offers a wide range of outdoor activities for nature lovers and adventure seekers, with its stunning coastline, parks, and waterways.
Kayaking & Paddleboarding in Casco Bay
Explore the scenic beauty of Casco Bay by kayak or paddleboard. The bay’s calm waters make it ideal for beginners and experienced paddlers alike. You’ll have the chance to see lighthouses, islands, and perhaps even some local wildlife like seals and seabirds. Renting equipment is easy, and guided tours are available if you’d like to learn more about the natural history and ecosystems of the area. Casco Bay offers the perfect outdoor escape.
Explore Portland’s History
Step back in time and uncover the fascinating history of Portland with visits to some of its most historic sites and landmarks.
Victoria Mansion
It is a stunning example of mid-19th-century architecture. Victoria Mansion (also known as the Morse-Libby House) is a beautifully preserved historic mansion that showcases Victorian-era design.
The house features opulent interiors which include intricate woodwork, hand-painted wallpapers, and original furnishings. It offers a fascinating glimpse into the lives of Portland’s wealthy elite in the 1800s.
Maine Historical Society
Learn about Maine’s past at the Maine Historical Society. It offers a variety of exhibits on state history, artifacts, and historical documents.
The Wadsworth-Longfellow House is also part of the society and provides insight into both the history of Maine and the life of poet Henry Wadsworth Longfellow. It’s a great place to dive into the state’s rich cultural heritage.
Eastern Cemetery
It is one of the oldest cemeteries in Portland. Eastern Cemetery is a fascinating place to explore for history buffs. It dates back to the 1700s, it’s the final resting place of many early settlers and notable figures.
The cemetery’s old gravestones and monuments reflect the early colonial history of Portland, and it provides a peaceful spot for reflection amidst the city’s busy streets.
7. Experience Portland’s Nightlife
Portland’s nightlife has something for everyone, from its vibrant craft beer scene to lively live music venues and cozy pubs. Explore local breweries like Allagash Brewing or Bunker Brewing Co., or enjoy creative cocktails at speakeasies like The Rum Club.
For live music, you can head to Port City Music Hall or One Longfellow Square, where you can catch local bands. If dancing is more your style, check out The Asylum or Empire for a night of fun. Afterward, grab a late-night bite at spots like Duckfat or Bramhall. It is perfect for satisfying your cravings.
Day Trips from Portland
Freeport (LL Bean & Outlet Shopping)
It is just a short drive from Portland. Freeport is famous for LL Bean’s flagship store and a variety of outlet shops. It’s the perfect spot for shopping, and you’ll find great deals on outdoor gear, clothing, and more.
Kennebunkport (Quaint Coastal Village)
It is known for its picturesque coastal beauty. Kennebunkport is a charming village with scenic views, beautiful beaches, and boutique shops. You can explore the quaint streets, enjoy fresh seafood at local restaurants, or simply take in the beautiful scenery at places like Goose Rocks Beach and Dock Square.
Acadia National Park (For Nature Lovers)
For a nature-filled adventure, head to Acadia National Park. It is just a couple of hours north of Portland. It is known for its stunning landscapes. The park offers hiking, wildlife viewing, and a beautiful coastline. Don’t miss the iconic Cadillac Mountain, where you can watch the sunrise and take in panoramic views of the park’s rugged beauty.
Where to Stay in Portland, Maine
If you’re planning to stay overnight in Portland, Maine here are two fantastic options that offer comfort, charm, and convenience for your visit:
The Francis Hotel & Spa
This boutique hotel provides a cozy and inviting atmosphere, with tastefully decorated rooms perfect for relaxation. After a day of exploring Portland, unwind by the fire in the main area or indulge in a spa treatment. The hotel also offers added perks like breakfast and coffee from the nearby Tandem Coffee shop. It is delivered straight to your room which ensures a peaceful start to your day.
The Press Hotel
It is located in the heart of Old Port. The Press Hotel is housed in a historic building that was once home to the Portland Press Herald. The hotel’s decor pays homage to its journalistic past, with thoughtful touches throughout the space.
The rooms are spacious and well-appointed which makes it a great place to rest after a day of sightseeing. You can also enjoy a delicious meal at the on-site Union Restaurant. It is known for its fresh seafood and vibrant atmosphere.
The Francis Hotel & Spa
This boutique hotel is a cozy, stylish choice for a stay in Portland. The rooms are tastefully decorated which creates a warm and welcoming atmosphere. If you’re looking to unwind, you can relax by the fire in the main area or treat yourself to a spa treatment. You can even have a delicious breakfast and coffee from the nearby Tandem Coffee shop delivered right to your room which ensures a relaxing start to your day.
The Press Hotel
It is located in the heart of Old Port. The Press Hotel is housed in a historic building that once served as the Portland Press Herald office. The decor reflects its history, with typewriter-inspired designs and vintage newspaper clippings.
The spacious, comfortable rooms are perfect for relaxing after exploring the city. Guests can also enjoy fantastic meals at the Union Restaurant. It offers a delightful dining experience just steps from your room.
The Alouette Beach Resort
If you’re looking to be closer to the beach, The Alouette Beach Resort is an excellent option. It is located along the coast of Old Orchard Beach. It offers stunning ocean views and is just a short drive from downtown Portland. The resort is family-friendly and has great amenities. This includes a heated outdoor pool, restaurant, and beach access. It’s a perfect spot for both relaxation and fun.
Portland Harbor Hotel
For those seeking a more luxurious experience, Portland Harbor Hotel provides an elegant stay in the Old Port district. The rooms are spacious and designed with a nautical theme. It reflects the city’s coastal heritage. On-site, you’ll find The Eve’s at the Harbor. It is a top-tier restaurant known for its seafood and upscale ambiance. It’s an ideal choice if you want to be in the center of the city’s vibrant dining and shopping scene while enjoying top-notch service.
How to Spend the Perfect Day in Portland, Maine
Start your day in Old Port by strolling through its cobblestone streets. Grab a coffee at a local café, like Tandem Coffee Roasters, and enjoy the vibrant atmosphere of this historic district. You can also explore the unique shops, boutiques, and art galleries lining the streets.
For brunch, head to Eventide Oyster Co.. It is known for its mouthwatering lobster rolls and fresh seafood. Afterward, take a short walk to the iconic Portland Head Light and soak in the breathtaking views of the coastline. It’s a must-see spot for any visitor.
In the afternoon, take a ferry ride to Peaks Island, where you can enjoy a peaceful escape, bike around the island, or relax on the beach. Alternatively, visit one of the many art museums, such as the Portland Museum of Art, or discover the thriving street art scene of the city.
For dinner, enjoy some of the finest seafood Portland has to offer at Scales, where you can savor fresh catches with beautiful waterfront views. After dinner, wind down at a rooftop bar like The Glass House which offers panoramic views of the city, or visit a local brewery for a nightcap to experience Portland’s craft beer scene.
End the night with a leisurely stroll along the waterfront or in one of the charming neighborhoods of Portland by enjoying the blend of history, culture, and natural beauty that makes this city so special.
Final Thoughts
Portland, Maine, offers an incredible mix of coastal beauty, rich history, and vibrant culture, making it a must-visit destination. Whether you’re exploring scenic lighthouses, indulging in fresh seafood, or strolling through the charming Old Port, there’s something for every traveler.
If you love exploring picturesque small towns, you might also enjoy the mountain charm of Gatlinburg or the breathtaking coastal views of Carmel-by-the-Sea. Plan your next adventure and discover the best of these stunning destinations!
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