A small town tucked between Falmouth and Brunswick along the Maine coast, Freeport offers plenty of shopping (including the flagship outpost of L.L.Bean and a huge range of outlets) along with hiking trails in the 200-acre Wolfe’s Neck Woods State Park.
Follow in the footsteps of Longfellow and visit his alma mater, Bowdoin College, in this historic and picturesque New England town. Maine Street has bakeries, shops, boutiques, antique shops, restaurants, and the Maine State Music Theater, which regularly features Broadway-quality performances.
Another year-round destination, Kennebunkport features numerous beaches, charming shopping along historic streets, and great spots for seafood. In the winter, a two-week-long Christmas Prelude takes over, leading HGTV to honor the city as No. 2 on its “Best Christmas Towns in America” list.
Ogunquit consistently ranks as one of the best places to visit on the Southern Maine coast. In addition to miles of sandy beaches, scenic coastline, and dramatic rocky cliffs, you’ll discover quaint colonial architecture, gorgeous tree-canopied streets, art galleries, and great shopping and dining.
A former mill town, Biddeford has been making waves recently with a slew of great new restaurants, wine bars, and breweries. Don’t miss Pepperell Mill, which has been transformed into a campus bursting with new businesses, shops, artist studios, and eateries.
1-2 Hours Away
The ultimate place to sample some of Maine’s best seafood, Damariscotta is said to source 80% of the fresh, farmed oysters in Maine. You’ll also find plenty of cozy shops, art galleries, and museums to explore in this quaint little town.
A postcard-perfect small town, Camden is well known for its gorgeous harbor and lively downtown—and it’s one of only two places on the Atlantic seaboard where the mountains meet the sea. Spend time exploring the shops, restaurants, and bakeries downtown, then head up to Mount Battie in Camden Hills State Park for incredible views over the water.
Once known for building ships, making lime, and carving out schooner loads of marble and granite, Rockland is now also known as a haven for the arts, music, and lots of lobster. Each summer, the Maine Lobster Festival attracts around 30,000 people for concerts, a parade, and a footrace across floating lobster crates.
The coastal town of Boothbay Harbor provides plenty of connection to the sea—whether you’re heading out on a whale, puffin or lobster cruise, or exploring the rich history of the harbor as an important fishing center.
Sitting on the Kennebec River, the capital of Maine provides plenty of scenic views, delectable dining options, beautiful historical buildings, and well-preserved history at the numerous museums.
2-3 Hours Away
A small village on the Blue Hill Peninsula, Brooklin is well-known for its picturesque bays and waterways. The town is also home to a distinguished arts community and the WoodenBoat School, which welcomes as many as 800 students to Brooklin every summer.
Considered one of the oldest towns in New England, Castine is a charming mid-coast Maine spot offering scenic views, plenty of history, and a wealth of activities, too: From golf and tennis to sailing and kayaking, hiking to the historic Dyce Head Light, visiting a historic museum, or seaside dining in the salt air.
Known as trophy-fish territory, Rangeley is a stunning area in Northern Maine surrounded by beautiful forests, mountains, and six lakes. A great place to see the stars, Rangeley features many Dark Sky Trail locations; in the winter, the popular Saddleback mountain draws plenty of skiers and snowboarders.
A small, rocky island 10 miles from the nearest mainland, Monhegan is perfect for a day trip to visit the lighthouse and the Monhegan Museum of Art & History, as well as savor the spectacular ocean views from the walking trails that cover the island.
As the largest of Maine’s offshore islands, Vinalhaven provides plenty of options from swimming to hiking to dining out. There are nearly two dozen parks and preserves scattered across the island, which are easy to walk or bike to during your visit.
3+ Hours Away
The gateway to Acadia National Park, Bar Harbor is a resort town with breathtaking ocean views, a vibrant downtown, and world-class water sports. Make sure to spend some time in the national park visiting some of the most popular attractions—including Cadillac Mountain, Sand Beach, Thunder Hole, and Otter Cliff.
Nestled on the rugged Maine coast, Lubec is the easternmost town in the continental United States. From unique landscapes to unforgettable experiences, this vibrant spot beckons you to explore the great outdoors. The Bold Coast Scenic Bikeway, a 211-mile route through the stunning natural scenery of coastal Maine, is one of the top attractions.
If you’re looking for a quieter section of Acadia National Park, this peninsula, hidden away on Maine’s mainland, is the perfect option. This peaceful section of rocky coast bordered by dense trees provides great walking paths, biking routes, and plenty of opportunities for solitude and quiet moments.