Summer in Harpswell, Maine.

The Best Small Towns in Maine for a Weekend Retreat

Over time, Maine has affectionately earned the nickname "Vacationland," a title that comes as no surprise to those who have made the trek to visit it. Beautiful shores, lush forests, shimmering lakes, and native wildlife abound, creating an atmosphere of untouched beauty. Charming little towns, steeped in history and brimming with stories passed down through generations, are tucked away within these natural wonders. As the weekend approaches, these towns come alive with a vibrant energy, beckoning travelers from far and wide who seek the perfect retreat from the hustle and bustle of everyday life.

Swan’s Island

A walkway in Swan's Island, Maine
A walkway in Swan's Island, Maine.

Swan’s Island is the ideal destination for a short weekend getaway. The 7,000-acre island is easily explorable within a couple of days. Stunning rocky coastlines and dense forests populate the island. The adventure begins during the journey to reach the island, which is accessible exclusively through the Maine State Ferry Service. Outdoor lovers can venture along the island’s 1.8-mile marked trails and explore its four public beaches, three of which require hiking for access.

Visitors can explore the island's rich history at the Swan’s Island Lobster & Marine Museum, showcasing artifacts from its fishing industry past. The Swan’s Island Historical Society offers additional insight through various exhibits. Those wanting to disconnect can stay at the Harbor Watch Inn, one of the Island’s few hotels.

Boothbay Harbor

Downtown Boothbay Harbor, Maine.
Downtown Boothbay Harbor, Maine. Image credit EQRoy via

Those who love spending the day out on the water will love Boothbay Harbor. Many travelers take to sailing, fishing, kayaking, or paddleboarding, enjoying the sea breeze and scenic views of the rocky coastline. The picturesque views continue, with travelers having various waterfront restaurants to select from, including McSeagull’s and 727 Ocean Sunset Bar.

The Coastal Maine Botanical Gardens, featuring over 300 acres of gardens, is also a Boothbay favorite. Charming bed and breakfasts line the downtown area, making it easy to find a place to spend the night. Harbour Towne Inn, a waterfront inn surrounded by lush gardens, will enchant visitors with Boothbay’s relaxed spirit.


The marina in Castine, Maine.
The marina in Castine, Maine. Image credit Kristi Blokhin via

Despite its modest population of just over 900, Castine's 400-year history, adorned with Greek and Federal Revival architecture, coupled with its enchanting harbor, promises an abundance of activities for a weekend escape. Castine does not shy away from recreational activities. Between sailing, kayaking, tennis, and golf, the town has a sport for everyone.

Visitors can also hike a short footpath around the Dyce Head Lighthouse, established in 1829. Shoppers can easily spend a Saturday afternoon strolling through Castine’s village of shops and galleries before stopping at a mouthwatering restaurant. Pentagoet Inn completes the Castine experience with its charming Queen Anne Victorian architecture. It also features a wine bar with delicious food and drinks!


A closeup of a seaplane in Moosehead Lake, Greenville, Maine.
A closeup of a seaplane in Moosehead Lake, Greenville, Maine.

Nestled alongside Maine’s largest lake, Moosehead Lake, Greenville emerges as an ideal hub for fishing, boating, canoeing, and hiking enthusiasts. Positioned amidst this expansive 40-by-20-mile lake, intrepid travelers can embark on a hike up Mount Kineo, a towering 763-foot cliff, to relish breathtaking 360-degree vistas from its summit. Lily Bay State Park, nestled on the shores of Moosehead Lake, offers ample room for swimming and boasts a sandy beach perfect for sun-seekers.

Wishing for a memorable excursion? Book a Moose Safari on Moosehead Lake to encounter majestic moose in their natural habitat. The Greenville Inn is an excellent place to stay. It showcases the town’s history through photographs and paintings splayed on the walls, accompanied by a well-preserved historic interior.


Aerial view of Rockland Harbor during Rockland Lobster Festival in summer, Rockland, Maine.
Rockland Harbor during Rockland Lobster Festival in summer, Rockland, Maine. Image credit Wangkun Jia via

Rockland has a plethora of activities, from summer festivals to island explorations and water sports. Every July, the renowned North Atlantic Blues Festival attracts visitors worldwide, showcasing acclaimed jazz performers like Jr. Wells and Koko Taylor alongside delectable seafood, embodying the essence of the Atlantic Coast. While most beaches in Rockland host rocky shores, Barrett's Cove on Megunticook Lake provides a rare sandy oasis for sunbathing and swimming without the usual crowds, even during peak summer.

For a sophisticated dining experience to cap off the day, 18 Central Oyster Bar & Grill stands out with its upscale ambiance and locally sourced seafood delicacies, ensuring a memorable culinary journey. Nestled in Rockland’s quaint historic district, the LimeRock Inn is a Victorian mansion converted into a cozy bed and breakfast that is a great lodging option for a short getaway.


Shoreline View of Lowell's Cove in Harpswell Maine
Lowell's Cove in Harpswell, Maine.

Harpswell stands out as a truly distinctive town, on Harpswell Neck, a cluster of sizable islands interconnected by bridges. The best way to become quickly familiar with Harpswell is by embarking on a kayak tour. Those who have always wanted to sail but have never known where to begin are in luck. Orr’s Bailey Yacht Club provides beginner sailing sessions that will take its students through racers to practice. Back on solid ground, Harpswell has lots of history to share. The colonial era Old Meeting House is a fascinating landmark, dating back to the 1750s and used by generations to host church services.

Additionally, a historic colonial burial ground lies just behind it. For hikers, Cliff Trail is a true gem. The rugged, 2.3-mile trail features stunning views overlooking 150-foot cliffs. Heading back into town for the night, The Harpswell Inn, dating back to the 1700s, offers a comfortable retreat at the waterfront.


Aerial view of buildings, a bridge, and forests in and around Rumford, Maine.
Overlooking downtown Rumford, Maine.

Fishers and hikers flock to Rumford in the summer months due to its scenic and relaxing surroundings. Androscoggin River becomes a haven as the weather warms, with locals and tourists participating in fishing, boating, and paddling. Those up for a challenge can hike up Rumford’s Whitecap Mountain, which has two trails that lead to panoramic views of the forests and hills below. Back in town, Rumford offers an array of antique, collectible, and thrift shops, making it easy to find a unique souvenir. The J. Eugene Boivin Park along the river is a great place to wrap up an afternoon before heading to your lodging. Hotel Rumford is a classic; a cozy stay right on the river.

Although travelers could easily spend beyond a month exploring Maine’s treasures, a weekend trip provides a fantastic taste of what this state has to offer. From coastal paradises like Boothbay Harbor to serene island escapes like Swan's Island, each destination represents a unique side of Maine’s rugged culture. As you prepare your weekend itinerary for some much-needed time away, do not shy away from these memorable destinations in Vacationland.

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