9 Of The Most Adorable Small Towns In Maine

Located in the northernmost reaches of New England, Maine is recognized as one of the most interesting and beautiful states in the nation. Home to over 4,600 islands, more than 60 lighthouses, and thousands of lakes and ponds, Maine has no shortage of adorable small towns. The charming coastal towns and the beauty which surrounds them are why Maine is known as ‘the land of remembered vacations,’ where memories are made. So, make sure to bring a camera and your sense of adventure, as Maine is a place that many people come to visit, but few ever truly wish to leave.

Boothbay Harbor

Surrounded by lighthouses and islands sits Boothbay Harbor, Maine. With a population of less than 1,000 people, this town has a picturesque setting, with a quaint walkable downtown area and charming Victorian architecture. Unique boutiques and numerous galleries are located throughout the town, adding to the flourishing art scene that makes it stand out. Some of the most beautiful places to visit in Boothbay Harbor include the Coastal Maine Botanical Gardens, a waterside spot that has approximately 250 acres of natural landscapes, trails, and manicured gardens, providing a perfect place to spend the day. Enjoy a whimsical dinner theatre performance at the Carousel Music Theatre; with great food and fantastic entertainment, there is little else you can ask for. Take a trip with Cabbage Island Clambakes boat tours, offering a unique experience cruising around Boothbay Harbor to Cabbage Island, where guests will enjoy a delicious clambake.

Damariscotta

Damariscotta, Maine, is a preserved coastal town where artistic beauty meets historic charm. Known for its original architecture and walkable streets, it has been ranked by Down East Magazine as one of the prettiest villages in the state. Damariscotta has numerous art galleries located throughout, each with a unique style that draws in visitors from across Maine. A historical piece of culture can be found at the Lincoln Theatre, housed in a circa-1875 building that shows classic and indie movies as well as theatre, concerts, and other events. Every Fall, the Damariscotta Pumpkinfest Event & Regatta takes place, where local artists transform giant pumpkins into whimsical works of art for all to enjoy. Be sure to visit the Whaleback Shell Midden State Historic Site, where you can stroll through a historic apple orchard and hike along the Damariscotta River.

Wiscasset

Wiscasset is located along the Sheepscot River and is known as the ‘prettiest village in Maine.’ Filled with old homes and churches as well as interesting shops and antiques, this charming waterfront town has a lot to offer. Aesthetically pleasing, there is plenty of scenic beauty and historical architecture to keep you busy, such as the 1970 Tiny House, a historical landmark that has been passed down through generations. Those looking for excitement can spend the day at Monkey C Monkey Do, an adventure sports center that features 6 zip lines and over 50 climbing structures. After a long day of exploring, be sure to stop by Sprague’s Lobster, a family-owned waterfront seafood restaurant, where its outdoor seating and decorated shacks exude charm and uniqueness.

Kennebunkport

Even the name brings out a smile as the charming town of Kennebunkport, Maine, has numerous activities that are sure to make you stop and bask in the moment. Kennebunkport is a small village that has unique galleries, where visitors feel like they are walking into a history book. An iconic landmark is the Goat Island Lighthouse, which is still active and accessible by boat. Established in 1883, in the summer it sits atop lush green grass, making it a beautiful sight. Relax at Goose Rock Beach, where the clear water and miles of white sandy beaches make it a popular place to watch the cute harbor seals soaking up the sun. Visit the Seashore Trolley Museum, which holds the title of the largest museum of mass transit vehicles. Exhibits are located both indoors and outdoors and include a miniature model railroad constructed by hand.

Rockport

Nestled between Camden and Rockland is Rockport, Maine, a coastal town that is known for its artistic community, historic lime kilns, and scenic harbor. Be sure to visit the Andre the Seal Statue, a historical landmark of a giant stone seal, which is to honor a male harbor seal named Andre that lived in Rockport and became a popular tourist attraction in the 1980s. A great place to spend the day is the Beech Hill Preserve, a 295-acre forested park and nature preserve that features two trails and a hilltop summit, perfect for those who want to catch the sunrise. If you are hungry, make sure to check out Nina June, where quality food meets breathtaking views, overlooking the coast as the boats seem to dance in the water.

Greenville

At the heart of the Maine highlands sits Greenville, a well-known town that has long attracted visitors due to its natural beauty and stunning views. Greenville looks more like a cottage area than a town, surrounded by mountains, lakes, and parks. Visitors can go on a cruise down Moosehead Lake on the last remaining steamboat in Maine, the Katahdin, built in 1914. Greenville also has Big Moose Mountain, for hiking and skiing, and Little Moose Mountain and Pond, a 4.3-mile loop trail that is popular for those seeking a moderately challenging hike. Lily Bay State Park has camp sites, boat launches, a small beach for swimming, and picnic areas, spread out across a 925-acre park that offers year-round activities.

Stonington

Another adorable town that is also Maine’s top lobster port is the town of Stonington, Maine. Stonington is a great example of Maine’s coastal charm, with thriving arts, natural beauty, and breathtaking landscapes. Surrounded by beauty, the town is home to several nature preserves, including Barred Island Preserve and Settlement Quarry Preserve, where visitors can spend the day hiking scenic trails, enjoying a quiet picnic, and spotting local wildlife. Visit Opera House Arts, where various performances and films are shown throughout the year in a historic venue, making every visit unique. For a closer look at the rugged coastline and its inhabitants, join Osprey’s Echo Sea Kayaking for a guided tour on the water. Along the way, you might catch sight of majestic eagles, ospreys, playful porpoises, and curious seals in their natural habitat.

Castine

Perched on Penobscot Bay in Hancock County, the town of Castine, one of New England’s oldest settlements, is known for its welcoming nature. With a population of around 1,000, this town is a great place for those wanting a scenic escape. Particularly intriguing is the fact that the entire town of Castine is on the National Register of Historic Places, making it a beautiful view of the past. Visit the numerous historical sites and landmarks, which include Fort Madison and Fort George Park, where remains of the late 18th century are still present. Near the mouth of Penobscot Bay, Dyce Head Lighthouse sits atop a rocky coastline; it is a picture-perfect setting looking out across the Bay. Explore by passenger cart with the Castine Touring Company and learn more about the town from knowledgeable tour guides.

Blue Hill

Blue Hill, Maine, is a place that seems to come straight out of a fairy tale, with its beautiful views, eclectic shops, and imaginative events. Check into the Blue Hill Inn, an adorable bed and breakfast located in the centre of town that offers guests a romantic escape that will long be remembered. Spend the day at Blue Hill Mountain, known for its hiking trails and scenic views of the town and surrounding area. If you are visiting in late August to September 1st, the Blue Hill Fair draws in people from all across Maine who go to experience a true country fair with some of the finest entertainment.

Adorable in their own way, whether it is the abundance of natural beauty, the charming members of the community, or the events, activities, and shops, each of these towns has a great assortment of quaint and cozy experiences. With approximately 89% of Maine forested, over 32,000 miles of rivers and streams, and thousands of lakes and ponds, each of the towns discussed has many fantastic opportunities to enjoy nature, offering visitors captivating opportunities to explore this wild and wonderful state.