7 Little-Known Towns In Maine

Averaging over 15 million visitors annually, Maine has a thriving tourism industry, drawn by its iconic lighthouses, rugged shorelines, and famous lobster. However, many tourists gravitate toward Maine’s national park and larger coastal cities, leaving some of the state’s best-kept secrets untouched. If you enjoy peaceful islands, freshly caught oysters, and cozy holiday celebrations, these seven, lesser-known Maine towns will not disappoint.

Castine

Castine, with a population of roughly 900 residents, lies in eastern Maine, in the Downeast Maine Acadia region, and is one of the state’s oldest communities. To appreciate a classic Maine lighthouse, visitors can explore the Dice Head Lighthouse, where the original keeper's house and barn remain on the premises, even though the lighthouse was discontinued in 1935.

In the winter season, Castine has lots of activities for visitors, such as snowshoeing and cross-country skiing. Cross-country skiers will enjoy skiing in Witherle Woods, a 185-acre preserve with beautiful views. For a charming place to stay, consider the Pentagoet Inn and Pub, located on a seaside bluff in a Queen Anne Victorian home, each room including a gourmet, country breakfast!

Swan’s Island

Swan’s Island, just southwest of Acadia National Park, spans 7,000 acres, making it easy to explore during a weekend away. Though it is home to 350 residents year-round, the population can increase to around 1,000 during the summer months. Visitors will feel a sense of disconnection from the mainland, as the island is accessible only by the Maine State Ferry.

To learn about the island’s rich history, travelers can stop by the Swan’s Island Lobster & Marine Museum, which contains a number of historic fishing artifacts, or the Swan’s Island Historical Society, which has various exhibits to explore. Regarding nearby natural attractions, there are four public beaches spread throughout the island and 1.8 miles of marked trails for hikers.

Rockland

Rockland, sitting along midcoast Maine, has a population of nearly 8,000 residents and is known for its thriving lobster fishing industry. As a result, the town is home to numerous seafood spots, with Archer’s on the Pier being a local favorite. This family-owned restaurant sits right on the water, offering the perfect spot to enjoy some crabcakes or poached lobster with a view.

The town’s vibrant art scene also provides plenty of entertainment, such as the Farnsworth Art Museum, which has a nationally recognized art collection of more than 10,000 works and rotating exhibits. Driving just 15 minutes north, visitors can reach the Camden Snow Bowl, which features 15 vertical runs for skiers and snowboarders, many of the trails having seaside views.

Damariscotta

Tourists flock to the southern Maine town of Damariscotta to try its renowned oysters. In fact, the region even hosts its annual Pemaquid Oyster Festival each fall to celebrate the local oyster industry, complete with an oyster shucking contest, food, music, and displays. Visitors can also enjoy an oyster and wine-tasting cruise along the Damariscotta River, where the boat passes by the local oyster farms during the journey.

Walking through the Whaleback Shell Midden State Historic Site, travelers can admire one of the largest intact middens along the eastern coast, which dates back thousands of years. For a more involved hike, travelers can explore one of the trails from the Coastal Rivers Conservation Trust, which offers an extensive network of approximately 50 miles of trails.

Waldoboro

Waldoboro, situated in Lincoln County along the Medomak River, is home to just over 5,000 residents and has a prominent agricultural scene that produces fresh foods and excellent local beer. One of the best places to get a taste of Waldoboro’s good food is the Odd Alewives Farm Brewery, a sustainable brewery and farm that serves craft beer and wood-fired pizza, open seasonally.

To try some delicious meats, cheeses, or sauerkraut, visitors must stop by Morse's Sauerkraut, which has been in operation since 1918. To see local artifacts and replicas, visitors can spend an afternoon at the Waldoborough Historical Society or appreciate an interesting collection of antique toys at Fawcett's Antique Toy and Art Museum.

Stonington

Stonington sits on the southern portion of Deer Isle, an island along Maine’s Atlantic coast, and is often considered the gateway to Merchant’s Row Archipelago, one of the country’s largest clusters of islands. In the warmer months, visitors can explore Deer Isle with Deer Isle Ocean Tours, offering private charters led by a knowledgeable captain. Every January, Stonington puts on its annual Winterfest event, which features a pickleball tournament, fireworks, dancing, food, and arts and crafts.

For a cozy stay, visitors can reserve a room at the Inn on the Harbor, a seaside inn offering views of Penobscot Bay and a history dating back to the 1880s. The Stonington Operahouse makes for a nice night out as well, built in 1886, featuring a variety of live shows and holiday activities.

Kennebunkport

Kennebunkport, considered a resort town for over a century, lives up to its motto, "the place to be all year.” Travelers must visit Kennebunkport in December when the town kicks off its annual “Christmas Prelude” event, which includes tree lightings, caroling, a fireworks display, Santa arriving in a lobster boat, and more!

The Edwin L. Smith Preserve, covering 1,100 acres, is a favorite among hikers in the summer with its babbling brooks, forests, and small bridges, and later transforms into a cross-country ski trail system during the winter months. Similarly, Goose Rocks Beach draws swimmers in the summer, but during the colder months, it quiets down into a peaceful winter wonderland, perfect for a serene walk along the shore. For a refined and luxurious stay, consider booking a room at one of the Kennebunkport Captain Collection Houses, which offer a selection of historic homes and mansions, each with individual rooms available for reservation.

Final Thoughts

Though less frequented than many of Maine’s well-known destinations, these towns have close-knit communities, rich histories, and beautiful natural landmarks that make them exciting choices for a getaway. To top it off, their locally sourced delights—like oysters, lobsters, and farm cheeses—guarantee a culinary experience that perfectly complements your visit. If you are ready to explore a different side of Maine, these off-the-beaten-path towns are the perfect starting point.