6 Picturesque Towns in Maine for a Weekend Retreat in 2024
The beautiful state of Maine has a long history of hospitality in New England. This is where you’ll find America’s oldest inn, its first chartered city, and some of the most visited parks in the country. It’s also the first state to see the sunrise every morning! These picturesque towns in the Pine Tree State are the ideal destination for a weekend getaway. Sit by the bay and watch sailing ships go by, visit one of Maine’s classic candy-striped lighthouses, stroll historic streets, hike lush Maine forests, take a winery tour — whatever your ideal weekend looks like, you’ll find it in these pretty Maine small towns.
Castine
In the heart of Downeast Acadia, Castine is a charming waterfront town with a rich maritime history, stunning streets lined with Victorian and Georgian architecture, and beautiful beaches. For the true Castine experience, stay at the Pentagoet Inn. This quaint Bed and Breakfast was built in 1894 and boasts gorgeous views over Penobscot Bay.
It’s easy to lose a few days in Castine. Spend an afternoon exploring the historic downtown, calling the Castine Historical Society and the Wilson Museum to get more information on the area. Then, turn your attention to the water. Castine Cruises offers day sails and sunset cruises on the bay, or you can walk to the historic Dyce Head Light near the mouth of the river. If the sea air makes you hungry for local shellfish, dine at the Safe Harbor restaurant at the Town Dock. The mouthwatering menu serves up local lobster rolls and fish sandwiches.
Stonington
Spend a weekend lounging on an island without having to leave the country with a visit to Stonington. Off the coast of Maine, this pretty town on the southern end of Deer Isle is connected to the mainland via a bridge. As you’d expect, this is a fishing town with plenty of water-based activities on offer. Rent a kayak and explore the island from the water, hop aboard a sightseeing cruise to see the coastline and say hello to the resident puffin population, or simply head for one of the island’s many pristine beaches.
More lobsters are landed in Stonington than in any other town in Maine, so don’t leave the island without getting close to the crustacean. Take a lobster fishing charter, or let others do the hard work and enjoy an entree at a fine dining hotspot in Aragosta. This farm-to-table restaurant is also a private resort where guests can book a luxury cottage with a view of the ocean.
Naples
If you’re looking for jaw-dropping scenery and outdoor adventure, Naples is the small town for you. In the heart of Maine’s lakes and mountain region, this is a year-round destination that offers excellent hiking and biking in the summer and world-class snowmobiling, ice-fishing, and skiing in winter. Visit in the fall, and you’ll catch the glorious autumnal colors of the changing leaves.
Stay on the shores of Long Lake and enjoy stunning views with your breakfast at the Lakeview Inn. This classic New England B&B is just steps from the water, but to really explore the lake, hop on the Songo River Queen. This replica paddle boat steamer offers narrated cruises along the lake. On a clear day, you can see the White Mountains of New Hampshire rising in the distance. Get more gorgeous views at nearby Sebago Lake State Park, where you can hike the trails, do some fishing, or simply hang out at the beach. After all that fresh air, head back into town to grab a bite and enjoy live entertainment at the Freedom Cafe overlooking the water.
Waterville
Waterville, in the Kennebec Valley, is a riverfront college town that began life as a mill settlement but is now a hub of arts and entertainment. Perfect for culture vultures, this vibrant community will keep you busy all weekend. Visit the Colby College Museum of Art, founded in 1959, to view nearly 8,000 pieces of contemporary and specialty works.
In downtown Waterville, you’ll find the Waterville Opera House, which hosts community theatre productions, comedians, musicians, and more. As you explore the downtown area, stop by the Waterville Farmers Market, which has been in operation since 2006 and is open year-round. From there, it’s just a short walk to one of Waterville’s most beloved historic attractions, the iconic Two Cent Bridge, which straddles the Kennebec River. If you’re looking for lodging downtown, try the Lockwood Hotel. Stylish and modern, this boutique hotel is right in the heart of Waterville, making it an excellent choice for weekenders.
Orono
Orono, in the Maine Highlands, is best known as home to the University of Maine. The college offers lots to do on a weekend trip, and you can even stay on campus at the inviting Hotel Ursa, a boutique hotel with modern amenities and a laid-back, welcoming vibe.
The university has a number of fascinating attractions that are open to the public. Visit the Hudson Museum in the Collins Center for the Arts to see its impressive display of world cultures through the ages. Star-gazers and amateur astronomists will love the Versant Power Astronomy Center, a planetarium and observatory that hosts regular events and educational workshops. The Page Farm and Home Museum is a popular stop for those wanting to learn about Maine’s agricultural history in the 19th and 20th centuries. This quaint specialty museum contains an 1833 post-and-beam barn, an 1855, one-room schoolhouse, a carriage house, a blacksmith shop, and a heritage garden.
Millinocket
Deep in the North Maine woods, you’ll find the scenic town of Millinocket. This small town is a magnet for outdoor enthusiasts, most coming to explore Maine’s largest state park. Baxter State Park covers over 200,000 acres, 215 miles of trails, 40 peaks and ridges, and the state’s largest peak, Mount Katahdin. Experienced hikers can make the 5,270 ft climb to the summit for breathtaking views. National Geographic highlighted the trail to the top as one of the best summit hikes.
From mountains to rivers. If you’ve ever wanted to try white water rafting, now’s your chance. Several tour companies in town offer rafting experiences on the rushing waters of the Penobscot River. If you need a break from all that adventure, head back into town to go shopping. Moose Prints Gallery and Gifts offers stunning landscape and wildlife prints that would make the perfect souvenir. Also, downtown, you’ll find the Gather Inn. A pretty, homespun B&B built in 1910. With comfortable rooms, a quaint parlor, a cozy library, and a wrap-around porch where you can relax after a long day on the trails, the Gather Inn makes the ideal basecamp for weekend warriors.
Escape to Maine’s Most Beautiful Weekend Retreats
Adventure, art, history, culture; it’s all waiting for you in Maine’s small towns. Come for the weekend, and these picturesque playgrounds will leave you wanting more — more lazy days on the river, more sunny afternoons exploring the wooded wilderness, more browsing boutique galleries, and fascinating exhibits. It’s no wonder over 15 million people visited Maine last year. Plan a weekend in the Pine Tree State, and you’ll be one of the many visitors eager to return.
