Maine Road Trip: Memorable Vacation Fun in Scenic Cities & Towns

Portland is the largest city in Maine and the perfect beginning to this extraordinary route. Portland’s downtown area is packed with culture and entertainment. Plus, Bon Appetit once named it Restaurant City of the Year, so be sure to come hungry. Portland’s rich history is alive in the Old Port District downtown, where cobblestone streets, 19th century architecture, eclectic boutiques and delicious restaurants meet the scenic waterfront and rustic fishing piers. Self-guided walking tours are a great way to see the sights. Follow the 3.25-kilometer Portland Freedom Trail to 13 historic sites influential in the anti-slavery movement, including stops on the Underground Railroad. Other walking tour topics include breweries, food and haunted Portland. In the neighboring East End, see the city and surrounding harbor at the Portland Observatory. The historic maritime signal station turned museum offers spectacular views from atop the 7-story structure. At the nearby Maine Narrow Gauge Railroad Co. & Museum, restored locomotives from the early 1900s take riders on a leisurely, 5-kilometer trip along the eastern shore. For some evening entertainment, the Portland Ballet, Portland Symphony Orchestra and Opera Maine all host classically trained performances. Thompson’s Point, Portland’s outdoor riverfront theater, is a must to watch some live contemporary music in the open air.

After your fill of Portland’s city charms, make time to witness some iconic Maine visuals as you drive the scenic route to your next destination. Head south of Portland to Cape Elizabeth to see the oldest lighthouse in Maine, now the Museum at Portland Head Light. For some family fun, continue to Old Orchard Beach, a resort town home to a beautiful stretch of sandy beach, a classic oceanfront pier with restaurants and Palace Playland, New England’s only beachfront amusement park.

From Old Orchard Beach, jump on Interstate 95 and drive south to another coastal gem, Ogunquit. The town’s name comes from the indigenous Abenaki language meaning “beautiful place by the sea.” Although Ogunquit Beach is consistently among TripAdvisor’s Top 25 Beaches in the USA, its delightful downtown also can’t be missed. Art enthusiasts flock to view the 3,000-piece permanent collection at the Ogunquit Museum of American Art, a stop on The Maine Art Museum Trail. For more art, head to the Ogunquit Art Association’s Barn Gallery, which runs workshops, exhibitions, events and auctions promoting Maine art and artists. The Ogunquit Playhouse theater is listed on the National Register of Historic Places and puts on live musical performances year-round. The town is also home to numerous LGBTQ+ owned and operated hotels, restaurants, bars and theatres, which welcome everyone to relax and enjoy all the attractions of this seaside escape.

From Ogunquit, drive two hours north along the coast and into the Maine countryside on Interstate 295 to Skowhegan. Skowhegan’s riverfront downtown is a nationally designated Main Street community and has 38 architecturally significant buildings, most built between 1880 and 1910. Sprinkled among the historic structures, keep an eye out for 21 pieces by folk art sculptor Bernard Langlais, including the 19-meter-tall, wooden “Skowhegan Indian” sculpture. Meander along five designated walking trails all accessible from downtown and ideal for discovering this small-town jewel. Don’t miss the Swinging Bridge, a historic pedestrian bridge across the Kennebec River. If you want to get out on the water, opportunities to boat, kayak, canoe or stand-up paddleboard are available from the riverfront parks. Unique places and events in Skowhegan include the Skowhegan History House, built in 1839, and the Margaret Chase Smith Library & Museum, devoted to Smith’s life as the first woman to serve in both houses of the U.S. Congress and the first woman nominee of a major party for the President of the United States. The area surrounding Skowhegan is renowned as one of the largest maple producers in the USA and that title is celebrated every March at Maine Maple Sunday, where you can learn about all things maple while enjoying sweet treats. Maine Grains is an active gristmill in downtown, open to free tours and a shop selling grain products made onsite. For a spooky evening on the town, catch a movie at The Strand Cinema, a historic theater that still shows the latest releases but is also known for ghost sightings.

For the final stop on this road trip, drive an hour east on U.S Highway 2 and Interstate 95 through natural beauty to Bangor. Can’t-miss sights in this city include another stop on The Maine Art Museum Trail: The Zillman Museum of Art. Affiliated with nearby University of Maine, it houses over 3,500 pieces of work, including originals from Andy Warhol and Pablo Picasso. Just down Main Street from the Zillman, you’ll find the Maine Discovery Museum, a children’s museum full of hands-on exhibits and family-friendly fun. Check out the Whitney Park Historic District, a residential area with 42 properties built between 1850 and 1910. Another historic attraction, the Cole Land Transportation Museum houses antique cars, trains, plows, military vehicles and more. To spend some time outside, head to the Bangor City Forest, home to 16 kilometers of trails for hiking, cycling and, in the colder months, cross-country skiing. It also serves as the entrance for the Orono Bog Boardwalk, an elevated 1.6-kilometer trail home to dozens of local bird species. In the evening, head to the historic Bangor Opera House, where the nationally recognized Penobscot Theatre Company puts on classic and new productions. Continue down Main Street and you’ll find two more major destinations, Darling’s Waterfront Pavilion, an open-air amphitheater used for concerts, and the Hollywood Casino Hotel & Raceway, one of two casinos in the state. When it is time for this remarkable trip to end, take a short drive to Bangor International Airport (BGR) or make the two-hour return trip to Portland to catch a flight home.