Any fan of the great outdoors will never want to leave Maine since it offers unending wilderness and an outstanding selection of year-round activities. However, the cities and villages of Maine also offer a wealth of creature comforts to aid travelers in unwinding, recharging, and relaxing. These locations offer outstanding cultural and entertainment opportunities on par with those found in the major New England metro areas nearby. From many major U.S. airports, travelers can connect to Portland International Jetport (PWM) and rent a car to begin a wonderful journey through Maine.

Portland: A Major City with Special Charms

The largest city in Maine, Portland, serves as the ideal starting point for this spectacular tour. The downtown region of Portland is teeming with art and entertainment. Come hungry because it was once crowned the Restaurant City of the Year by Bon Appetit. In the Old Port District downtown, where cobblestone streets, buildings from the 19th century, unique shops, and mouthwatering restaurants converge with the picturesque waterfront and rustic fishing piers, Portland’s rich history is alive and well.

Walking tours that are self-guided is an excellent way to experience the city. Visit 13 significant anti-slavery historical sites, including stops on the Underground Railroad, along the 3.25-kilometer Portland Freedom Trail. Other themes covered on walking tours include Portland’s breweries, cuisine, and ghosts. View the city and surrounding harbor from the Portland Observatory in the nearby East End.

From the top of the seven-story building, the former maritime signal station turned museum offers breathtaking vistas. Riders can enjoy a leisurely 5-kilometer tour along the eastern beach on refurbished early 1900s locomotives at the neighboring Maine Narrow Gauge Railroad Co. & Museum. The Portland Ballet, Portland Symphony Orchestra, and Opera Maine all present classically trained performances as evening entertainment. If you want to listen to live contemporary music outside, you must visit Thompson’s Point, Portland’s outdoor riverfront theater.

Ogunquit: A Seaside Town with a Variety of Land Activities

After you’ve had your fill of Portland’s attractions, take a moment to take in some classic images of Maine as you proceed down the scenic path to your next location. Visit the oldest lighthouse in Maine, which is now the Museum at Portland Head Light, by traveling south from Portland to Cape Elizabeth. Continue to Old Orchard Beach for some family entertainment. This resort town is home to a lovely stretch of sand, a classic oceanfront pier with restaurants, and Palace Playland, the only beachfront amusement park in New England.

Take Interstate 95 south from Old Orchard Beach to Ogunquit, another seaside treasure. The name of the town is derived from the Abenaki language of the locals and means “beautiful location by the sea.” Ogunquit Beach is frequently ranked among the Top 25 Beaches in the USA on TripAdvisor, but the town’s charming downtown is equally worth visiting. Art lovers throng to the Ogunquit Museum of American Art, a stop on The Maine Art Museum Trail, to examine the 3,000-piece permanent collection.

Visit the Ogunquit Art Association’s Barn Gallery for additional artwork. This venue hosts workshops, exhibitions, events, and auctions to support Maine art and artists. The Ogunquit Playhouse theatre hosts live music events all year long and are listed on the National Register of Historic Places.

Historical, eerie, and outdoor attractions in Skowhegan

Take Interstate 295 for two hours north from Ogunquit to Skowhegan, traveling along the ocean and through rural Maine. With 38 aesthetically noteworthy buildings, the majority constructed between 1880 and 1910, Skowhegan’s riverfront downtown has been recognized as a Main Street community on a national level.

Look for 21 works by folk artist Bernard Langlais, including the 19-meter-tall wooden “Skowhegan Indian” sculpture, scattered among the old buildings. Explore this small-town gem by meandering along one of the five designated walking trails, all of which are accessible from the downtown area. The historic Swinging Bridge spans the Kennebec River and is a must-see attraction. The riverfront parks offer possibilities to the boat, kayak, canoe, or stand-up paddleboard if you want to get out on the water.

The 1839-built Skowhegan History House and the Margaret Chase Smith Library & Museum, both of which focus on Smith’s life as the first woman to serve in both chambers of Congress, are both noteworthy locations and occasions in Skowhegan. Congress as well as the first female presidential candidate from a major party. Every March, Maine Maple Sunday honors the region around Skowhegan as one of the nation’s top maple producers. Guests can learn about all things maple while indulging in delectable treats.

Bangor: A College Town With Lots of Activities, Attractions, and Art

Drive an hour east on Interstate 95 and US Highway 2 to reach Bangor, the destination of this road trip. The Zillman Museum of Art, a destination on The Maine Art Museum Trail, is one of the city’s must-see attractions. It is associated with the nearby University of Maine and has over 3,500 works in its collection, including originals by Pablo Picasso and Andy Warhol.

Near the Zillman, on Main Street, is the Maine Discovery Museum, a children’s museum with interactive exhibits and family-friendly entertainment. Visit the Whitney Park Historic District, a neighborhood of 42 houses constructed between 1850 and 1910. Visit the Bangor City Forest for 16 kilometers of hiking, biking, and, during the colder months, cross-country skiing trails if you want to spend some time outside. It also serves as the entrance to the elevated 1.6-kilometer Orono Bog Boardwalk, which is home to numerous native bird species.

In the evening, visit the storied Bangor Opera House to catch a performance by the nationally acclaimed Penobscot Theatre Company. Two more important locations are located further down Main Street: the Hollywood Casino Hotel & Raceway, one of the state’s two casinos, and Darling’s Waterfront Pavilion, an outdoor concert venue.