15 Best Things to Do in Portland, Maine That Only Locals Know

As the leaves turn golden and the crisp autumn air sets in, New Englanders know that it’s the perfect time to explore the quaint coastal city of Portland, Maine. With its rich maritime history, stunning waterfront, and a thriving arts and food scene, Portland is a treasure trove of activities and attractions that will leave you enchanted and eager to return.

From wandering the cobblestone streets of Old Port, lined with unique boutiques and eateries, to sampling the freshest seafood at one of the many local restaurants, Portland is a city that effortlessly blends tradition and innovation.

Whether you’re a history buff, a foodie, or simply looking for a relaxing getaway, Portland has something for everyone, and in this article, we’ll delve into the top things to do and see in this charming coastal city.

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Visit the Portland Head Light

Perched on the rugged cliffs of Cape Elizabeth, the Portland Head Light is one of the most photographed lighthouses in America. Built in 1791, this historic lighthouse offers breathtaking views of the Atlantic Ocean and the surrounding landscape. You can explore the surrounding Fort Williams Park, which includes walking paths, picnic areas, and remnants of old military structures, making it an excellent spot for family outings.

Explore the Old Port District

The Old Port District in downtown Portland boasts cobblestone streets lined with charming boutiques, art galleries, and seafood restaurants. This historic area retains its 19th-century architecture while providing a vibrant shopping and dining experience. Don’t miss the local shops featuring handmade crafts and the myriad of trendy bars where you can sample Maine’s famous craft beers.

Take a ferry to Peaks Island

A short ferry ride from Portland’s waterfront will take you to Peaks Island, a serene getaway known for its beautiful views and slow-paced lifestyle. Once there, rent a bike or golf cart to explore the island’s scenic sandy beaches, picturesque houses, and breathtaking ocean vistas. It’s an ideal spot for a relaxing day trip, with cafes and picnic areas perfect for enjoying a packed lunch.

Visit the Portland Museum of Art

The Portland Museum of Art is the largest art museum in Maine, showcasing an impressive collection of American, European, and contemporary art. Notable works include pieces by Winslow Homer and Andrew Wyeth, as well as modern exhibitions highlighting local artists. The museum’s architecture, which combines historic and modern elements, is as captivating as the art within its walls.

Stroll through Eastern Promenade Park

Eastern Promenade Park offers stunning views of Casco Bay and the Portland skyline. It’s a popular destination for walking, jogging, and picnicking, with well-maintained trails and ample green space. In the summer, watch for sailboats and ferries navigating the waters, and be sure to visit the nearby beach area!

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Learn about maritime history at the Maine Narrow Gauge Railroad Museum

This unique museum celebrates the history of Maine’s narrow gauge railroads through displays, artifacts, and vintage train rides. Visitors can experience a taste of what it was like to travel on these historical trains while enjoying views of the waterfront. The museum offers special events and hands-on activities that provide insight into a fascinating part of Maine’s transportation history.

Indulge in seafood at Luke’s Lobster

Widely regarded as one of the best spots for fresh seafood in Portland, Luke’s Lobster serves up sustainably sourced lobster rolls, crab rolls, and shrimp rolls. The casual atmosphere paired with the quality of their seafood makes for a delightful dining experience. Pair your meal with their homemade chowder or one of their refreshing beverages to complete your maritime feast.

Visit the International Cryptozoology Museum

This quirky museum is dedicated to the study of hidden and unknown animals such as Bigfoot and the Loch Ness Monster. With a collection of cryptid artifacts, exhibits, and local lore, there’s plenty to spark your curiosity. The museum offers a unique blend of science and fantasy, making it a fun stop for families and those who appreciate the bizarre.

Discover Fort Gorges

Located on a small island in Casco Bay, Fort Gorges is a Civil War-era fortification that remains relatively untouched. Accessible only by boat, this historic site features remarkable masonry and provides expansive views of the bay. Exploring the fort’s tunnels and barracks offers a glimpse into the past, plus the solitude of the island enhances the adventure.

Experience the Farmers’ Market at Deering Oaks Park

Every Saturday during the growing season, Deering Oaks Park hosts a bustling farmers’ market where local vendors offer fresh produce, baked goods, and artisanal products. This community event is a great way to taste locally sourced foods and engage with Maine’s agricultural scene. Be sure to arrive hungry—many vendors offer delicious samples!

Catch a show at the Merrill Auditorium

Home to the Portland Symphony Orchestra and various theatrical productions, the Merrill Auditorium is a cultural hub in the city. The auditorium hosts performances ranging from classical music to contemporary acts, ensuring there’s always something happening. Its elegant architecture and excellent acoustics provide a fantastic environment for enjoying live performance.

Explore the Victoria Mansion

The Victoria Mansion, also known as the Morse-Libby House, is a remarkable example of Italianate architecture and offers a glimpse into the opulent lifestyle of the 19th century. Guided tours showcase the mansion’s stunning interiors, including intricate plasterwork and exquisite furnishings. The mansion frequently hosts special events and exhibitions, making it a vibrant part of Portland’s cultural scene.

Walk the Old Port Waterfront

The bustling waterfront area of the Old Port offers a blend of scenic views and vibrant activity. Stroll along the piers and watch the fishing boats come and go, or relax at one of the many waterfront bars and restaurants. This area is especially lively during the summer months, with artists performing and various festivals taking place near the water.

Visit the Children’s Museum & Theatre of Maine

This interactive museum is designed for children and families, featuring hands-on exhibits, creative play areas, and engaging theatre performances. Kids can explore everything from a pirate ship to an art studio, making this an ideal destination for families seeking educational fun. The museum also hosts seasonal events and special programming to keep young minds stimulated.