Linekin Bay Resort

Your Guide to 5 of the Best Small Towns in Maine

The state of Maine is a place for exploration and discovery. Families travel here time and time again to immerse themselves in the nostalgic places and traditions that they find here. That is why guests of the time-honored Linekin Bay Resort recognize Boothbay Harbor as one of the best small towns in Maine! Once guests arrive at Linekin Bay Resort, they realize they have everything they need. However, there are a few other great small towns near Boothbay Harbor worth exploring on day trips from the resort.

There is so much to do and see in Maine that planning an itinerary can be overwhelming. Until August 25th, our all-inclusive resort provides guests access to our lodging, dining, sailing instructionkids’ camp, and much more. If guests seek more fun activities like exploring the best small towns in Maine, they turn to our useful Boothbay Harbor Vacation Guide! Within the guide is an extensive list of our best recommendations for things to do in Boothbay Harbor, so all guests have to do is take their pick.

5 of the Best Small Towns in Maine

Boothbay Harbor

The Midcoast Maine town of Boothbay Harbor is the perfect place to escape the hustle and bustle of daily life. Nicknamed “The Boating Capital of Maine,” this quaint seaside gem is ideal for unplugged family vacations. Between its proud history, charming local shops, delectable dining and world-renowned boating, there are all kinds of memories to be made in Boothbay Harbor. The east and west sides of the Harbor are connected by a long footbridge, so it’s easy for visitors to wander and explore cool coves, rocky beaches, and historic lighthouses. The residents of Boothbay Harbor are also known for their warm and friendly nature. What are you waiting for? Start planning your trip to Boothbay Harbor!

Round Pond

Just a 40-minute drive from Linekin Bay Resort, Round Pond is one of the best small towns in Maine because of its hospitality and coastal charm. Walking the streets of Round Pond feels like stepping back in time. The town is full of antique shops and seafood restaurants, but outdoor enthusiasts come for the Round Pond Public Preserved Land. Hikers walk around this area’s serene lake, hoping to catch a glimpse of the area’s abundant wildlife. The Marshall Point Lighthouse near Round Pond is also worth exploring.


Rockport’s small-town appeal is frequently celebrated. It is just under an hour away from Boothbay Harbor, so it makes for a perfect day trip. Fun for the whole family can be found here, including tours of Penobscot Bay and visits to Aldermere Farm, where visitors observe Belted Galloway (“Oreo Cookie”) cows grazing on sustainable farmland. Rockport is also a popular spot for harborside picnics and fishing.


For those who don’t mind traveling a few hours away from beautiful Boothbay Harbor, Stonington, ME, is a great day trip destination. People refer to Stonington as one of the best small towns in Maine for its boating, fishing, and art scenes. The Haystack Mountain School of Crafts features local artwork and there is always an engaging performance held at the Stonington Opera House. Both natural beauty and modern entertainment draw people to Stonington!


Castine, ME, is one of the oldest towns in the state and an easy choice for day trips. It is small enough to feel hidden away, yet bustling enough for families to keep busy on their visit. Castine’s Main Street slopes downward toward the sea and features plenty of shopping and entertainment. Historic homes and churches boasting traditional New England architecture populate this small town, so admiring it by foot is a must. Additionally, the Wilson Museum is a great place to experience the colonial history of New England. Castine, ME, is just over two hours away from Boothbay Harbor. A Maine coast map or Maine towns map can be helpful in charting your course for a trip through Castine and more of the best small towns in Maine.

Linekin Bay Resort is the Best Place to Stay in Maine

If you’re looking for a town central to everything Maine has to offer, look no further than Boothbay Harbor. It is one of the best coastal towns in Maine to live in and vacation in! Seaside lodging at Linekin Bay Resort often brings visitors to the area with its rustic charm and array of fun things to do for all ages!

The Beacon cabin is a great Boothbay Harbor hideaway for a family of up to six people. This three-roomed, wooded cabin is newly built and features a living room, pullout sofa, king bedroom, and extra bedroom with two full beds. Guests love this cabin’s deck, mini fridge, and private bathroom!

small towns in maine


Linekin Bay Resort is the best way to begin a Maine vacation through these wonderful small towns. What will you discover here?

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