With a jam-packed calendar of celebratory events, historic landmarks, and distinctive art, celebrate Maine’s distinctive history, creative people, and marine culture. You’ll come away from this road trip with fond memories, inspiration, and knowledge of how the land and water influenced the development of this incredibly creative location. Start this memorable arts and culture tour along Maine’s stunning coastline by taking a connecting flight to Portland International Jetport (PWM) from the majority of the region’s major airports. From there, rent a car and begin your journey.


Portland: Maine’s largest city’s urban art scene

Begin your tour in vivacious, scrollable Portland, set against the shimmering Casco Bay. The nonprofit Greater Portland Sites offers self-guided and volunteer-led tours of historic landmarks and attractions, including the notable Portland Observatory, a former maritime signal tower that is now a museum with a viewing platform, to enable tourists to experience the sights.
The galleries, theatres, museums, and educational institutions in the Arts District can keep you occupied for days. It’s a creative area that spans several city blocks and tries to offer all artists a chance to shine. Shaw Sculpture Park, one of nine museums on The Maine Art Museum Trail, houses more than 18,000 pieces by artists like Andy Warhol, Claude Monet, Pablo Picasso, and others.

Swing by Maine College of Art & Design’s Institute of Contemporary Art. Five shows, as well as several public events, artist talks, and graduate student exhibits are presented annually by this vibrant museum. The Maine Jewish Museum features both rotating exhibits that rotate every six weeks and permanent art collections.

Plan your trip to coincide with a First Friday Art Walk, when you may meander through streets crowded with local performers, musicians, and artists while also enjoying free admission to galleries, museums, and other art venues. Catch a performance at the Portland Stage Company for additional information about the performing arts scene.

This professional theatre produces amazing live performances all year long, including the Theater for Kids, which caters to audiences between the ages of 4 and 10. Additionally, Portland Ovations presents a wide variety of performances, including ballet, opera, Broadway, dance, jazz, and pop music. Explore off-the-beaten-path art institutions like Mayo Street Arts, a former church that now serves as a creative space for young people in Portland and hosts the annual International Puppet Festival.

Maine Trip

Historic Downtowns in Brunswick and Bath are Active

The picturesque riverfront downtown of Brunswick, which is less than an hour’s drive northeast of Portland, is recognized as a National Main Street. Walk across the Androscoggin Swinging Bridge, a pedestrian suspension bridge constructed in 1892 for Cabot Mill workers, for a picture-perfect promenade. Although the view of the river below is lovely all year round, the pinnacle of the fall foliage is when it is most mesmerizing.

The Bowdoin College Museum of Art houses more than 25,000 works of art created by artists from all over the world and is perpetually free and open. Your second destination on The Maine Art Museum Trail is housed in an 1894 structure that is listed on the National Register of Historic Places. Catch a variety of performances and events at the Maine State Music Theatre on summer evenings, including touring productions, musicals, concerts, and children’s theatre programs. The theatre has been in operation since 1959.

The Bowdoin International Music Festival is a six-week summer concert series that features more than 20 performances by the best classical musicians. The Peary-MacMillan Arctic Museum is the only museum devoted to arctic studies and exploration along the entire United States Trail, making it a truly exceptional experience.

The Maine Maritime Museum is located in Bath, another National Main Street, which is ten minutes away and is located on the banks of the Kennebec River. In addition to five original buildings from the 19th century and displays and relics from 400 years of shipbuilding, this museum contains the sole remaining wooden shipyard in the United States. Wyoming, a full-size reproduction of the biggest wooden sailing vessel ever constructed in North America, is a part of the collection.

The sculpture is also the biggest in New England. The replica of the 1607 pinnace Virginia, commonly regarded as the first ship constructed by Europeans in the New World, known as Maine’s First Ship, can be found above.

maine trip

Boothbay to Damariscotta: Artistic Coastal Communities and Wildlife Observation

Pick up a one-of-a-kind work of art at Edgecomb Potters in Boothbay, just a short 40 minutes away, after learning about Maine’s maritime heritage. Since 1976, it has been run by a family and sells a diverse assortment of jewelry made by hand in Maine as well as glass, metal, and wood crafts. Sheepscot Pottery, Watershed Center for Ceramic Arts, Georgetown Pottery, and AE Pottery is a few further famous pottery studios in the region.

Get lost among 102 hectares of towering wooden trolls at the Coastal Maine Botanical Gardens, which also offers seminars, talks, and parties. Take a boat cruise with Cap’n Fish’s Cruises and unwind along beautiful Boothbay Harbor.

Take a ferry or a boat charter to Monhegan Island, a National Natural Landmark, for a day trip that combines art, history, and sailing. Monhegan Island is famous for its artist colony that dates back to the mid-19th century and the Monhegan Island Lighthouse. Visit the Monhegan Museum of Art & History, another site along The Maine Art Museum Trail, to see the traditional portrayals of Maine.

Return to the mainland and travel 30 minutes to Damariscotta via the Damariscotta River. One of more than 80 locations on The Maine Oyster Trail, Glidden Point Oyster Farm offers tours where visitors may learn about and enjoy real Maine shellfish. Additionally, seals may be seen playing in the tidal playground. Colonial Pemaquid State Historic Site, which is home to the restored Fort William Henry, is another important attraction close to Damariscotta. Explore archaeological relics from the 17th and 18th centuries as well as the on-site museum that displays things discovered.

maine trip

Region of Rockland and Camden: Small Towns, Big Impression

Start the last leg of your journey at Rockland, which, despite its diminutive size, is home to the Center for Maine Contemporary Art, the Langlais Sculpture Preserve, and the Farnsworth Art Museum. Several of Bernard Langlais’ enormous wooden sculptures are kept in the Langlais Sculpture Preserve in Cushing. The Farnsworth Art Museum in Rockland, which is your final destination on the Maine Art Museum Trail, focuses on American art and has an internationally renowned collection of more than 10,000 pieces.

The museum also owns the 14-room colonial farmhouse, the Olson House, which is located in Cushing, about 30 minutes away. Visit the Owls Head Transportation Museum to see more than 200 vintage cars, motorcycles, and airplanes that were built before 1940. Go to Owls Head State Park next, where you can find the Owls Head Lighthouse, a peaceful picnic area, and a small rocky beach.

The American Lighthouse Foundation operates an on-site interpretive center where you can learn about Maine’s lighthouses and maritime mysteries full of ghost stories and shipwrecks. Catch a movie, a musical, or a play at The Strand Theatre in the evening. It was built in 1923 and is a National Register of Historic Places listing.