8 Romantic Small Towns In Maine For A 3-Day Weekend
A romantic weekend in coastal Maine can be as simple as a sunset sail out of Camden or a quiet loop on Acadia’s carriage roads in Bar Harbor. These eight small towns were chosen for walkable downtowns, good food, and highly rated inns that make a three-day stay easy. Most have a compact waterfront where you can browse small shops, pop into a gallery, and end the day with seafood and a glass of wine, with stops like Boothbay Harbor’s footbridge or the fish ladder at Damariscotta Mills giving you something specific to build an afternoon around. It’s a relaxed list designed for couples, empty nesters, and retirees who want beautiful views, good meals, and towns that still feel easy to explore on foot.
Bar Harbor
Bar Harbor offers visitors beautiful scenery, waterfront views, and access to Acadia National Park, which has 158 miles of hiking trails. Take a drive on the 27 miles of historic motor roads, or enjoy a hike on one of the trails. Acadia National Park also offers visitors the opportunity to explore on horseback on the carriage roads. With 45 miles of carriage roads, visitors can either take a guided carriage ride with Wildwood Stables or explore the carriage roads with their own horse. Visitors can also go stargazing at select locations. Stay at Bar Harbor Inn and Spa, which offers easy walking access to downtown shops, art galleries, and waterfront views. Enjoy fine dining at the Reading Room Restaurant, ocean views, and rejuvenating luxury spa services.
Bar Harbor’s long history adds to the range of things to see and do in town. For a unique experience, take a ghost walking tour with the acclaimed Bar Harbor Ghost Tours. Bicycle around the car-free carriage roads, or park loop roads with Acadia Bike & Coastal Kayaking Tours, or take a relaxing stroll downtown and enjoy boutique shops and art galleries.
Camden
Known as the “jewel of the Maine Coast,” Camden is a small New England town set along Penobscot Bay. Popular in the summer for family vacations, Camden is also the perfect spot for a romantic weekend any time of the year. Downtown Camden is easy to explore on foot, with boutique shops and small eateries along the harbor streets.
Take a sunset stroll along the waterfront overlooking Penobscot Bay, or take a sunset sailing cruise. For a cozy romantic getaway, stay at the Grand Harbor Inn. Enjoy a continental breakfast in your room each morning, and include a spa package for a couples' massage at Camden Maine Massage Therapy for the ultimate couples' relaxation. Enjoy Maine’s natural beauty and fresh air on the Mount Battie trail. You can also drive to the top of the mountain from the Camden Hills State Park to see the views from the top.
Kennebunkport
Founded in 1653, Kennebunkport has evolved from a simple shipbuilding village into a holiday destination. Enjoy fresh lobster at Nunan’s Lobster Hut, which has been serving lobsters to locals and visitors since 1953. Kennebunkport’s Dock Square is filled with locally owned shops selling candy, jewelry, clothing, and coastal home goods. Take a beach walk on Goose Rocks Beach, a 3-mile beach in Kennebunkport. Experience life in a coastal town with a boat ride and Lobster Tour, and learn about the local lobster industry while getting a unique view of Kennebunkport from the water. Or, experience an authentic schooner experience on the Schooner Eleanor with Captains Rich and Kris Woodman.
Kennebunk
Roughly a 10-minute drive away from Kennebunkport, Kennebunk offers visitors even more seaside views and waterfront experiences. Downtown Kennebunk has a mix of small restaurants, cafés, and local shops within a compact walkable area. Grab a coffee in the morning, and a glass of wine in the evening at The Blue Coffeehouse & Wine Bar before exploring the shops and sights. Stay in the Kennebunk Inn and Tavern, which dates back to 1799 when it was a private residence. With over 200 years of history, the Kennebunk Inn and Tavern is close to nature preserves, museums and galleries, antique shops, and more. The historic Tavern boasts a menu that blends local ingredients with favorites such as traditional Maine lobster rolls and other fresh seafood.
Boothbay Harbor
Boothbay Harbor is rich in history and offers plenty of sightseeing opportunities. Built in 1901 and now a historic landmark, the Boothbay Harbor Footbridge is a 700-foot wooden walkway that connects one side of the harbor to the other. The footbridge has recently been restored and rebuilt, and it is now the perfect spot for romantic walks at sunset, lit by the string lights spanning the bridge. Go back in time and take a vintage train ride on a steam locomotive at the Boothbay Railway Village Museum. While there, check out the Antique Automobile Museum, which has over 60 vehicles on display ranging from 1902-1962. Catch a show at The Opera House at Boothbay Harbor, which stages regional and national touring musicians, and is the perfect place for an evening of classical, Celtic, jazz, folk, R&B, bluegrass, and more. The historic upstairs bar provides a quiet place for a drink after a show.
Wiscasset
Known as one of the prettiest villages in Maine, Wiscasset is a historic Lincoln County town on the Sheepscot River, featuring 19th-century architecture. Wiscasset is the perfect town for a short getaway or to reconnect with your partner. There are numerous historic homes and museums to visit, including the Lincoln Court Museum and the
1811 Old Jail. Take a walk through the neighbourhoods of beautiful old houses and stop along the way to learn about Wiscasset’s rich history from the 32 Museum in the Streets signs, which take visitors on a self-guided walking tour of historic locations and architecture. While many come to Wiscasset for Lobster Rolls at Red’s Eats, other popular spots include Sea Basket and The Maine Tasting Center, where visitors can take workshops to learn about cooking with Maine’s fresh seafood.
Damariscotta
Enjoy small-town midcoast Maine charm and Pemaquid oysters in this slow-paced, intimate coastal town. Damariscotta’s name is derived from the Algonquian word “madamescontee,” which means “place of abundance of alewives.” Every year, to celebrate the running of these small, salty fish, which are used for lobster bait and are smoked and eaten, Damariscotta Mills hosts a “Run with the Alewives” 5K (3.1 miles) run in late May. The run includes cash prizes and a beautiful course along the Great Salt Bay. Throughout the year, you can visit the Damariscotta Mills to see the incredible fish ladder, but mid to end of May is the best time to see fish swimming. The fish ladder was originally built in 1807. This newly restored structure is used by the fish to return from the Atlantic Ocean to the Damariscotta Lake each year.
There are several year-round trails and walking paths in and around Damariscotta, including the popular Salt Bay Farm, which is three miles of trails in meadows along Salt Bay, and Huston Landing, a short 0.4-mile trail to a stunning view of the Damariscotta River. Grab some Pemaquid oysters from The Shuck Station, or for a more upscale experience, the Damariscotta River Grill, for a romantic dinner for two.
Monhegan Village
For an intimate, off-the-grid retreat, Monhegan Village is the perfect spot for sunsets, cliffside walks, quiet beach picnics, and exploring art studios and galleries. Located on a small island 12 nautical miles off the coast of Maine, Monhegan is a car-free fishing and artist community with a history spanning roughly 400 years. With nine miles of hiking trails that lead to some of the highest ocean cliffs on the Maine coastline, enjoy beautiful ocean views, good food, and quaint guest houses or full-service hotels. Stay at The Island Inn, located right on a bluff overlooking Monhegan Harbor, and enjoy the Dining Room for harbor views and fresh, local Maine cuisine. Explore the lighthouse, established in 1824 and now automated, for views of the village, harbor, Manana Island, and the mainland. Lighthouse Hill is also a great spot for a picnic, as long as you dress for the weather! Downtown Monhegan is full of art and inspiration. Visit the Monhegan Museum of Art and History to see local artists and learn more about the history and legacy of this small village.
A Romantic Coastal Retreat in Maine
A three-day weekend on the coast goes better when you choose one town and let it carry the whole trip. Settle into a comfortable inn, keep the schedule light, and return to the same waterfront walk or downtown streets each evening. Spend the days on simple pleasures, browsing a few shops, stopping into a gallery, taking a short trail, and stretching dinner into the night. The goal is not to cover ground, it’s to slow down together in a town that feels easy to navigate and worth lingering in.
