8 Perfect Destinations for a Long Weekend in Maine

Maine is a classic New England state with coastal and historic charm. Its idyllic scenery, cozy restaurants, and unique lodging options make it a perfect destination for a long weekend. Many small towns, with crisp air and traditional architecture, are walkable and enjoyable to explore.

Maritime history is rich in towns like Bar Harbor, and the natural scenery throughout the state in the fall is jaw-dropping. The downtown areas offer many shopping opportunities and quaint architecture that feels like stepping back in time. Many small villages dot the landscape and provide a unique destination for a leisurely vacation, relaxing, and discovering new places.

Bar Harbor

Bar Harbor is a famous sea harbor on Mount Desert Island in Maine's Frenchman Bay. The natural landscape is astounding and features Cadilac Mountain and Acadia National Park. The mountains wrap around Sand Beach, which provides views of the Porcupine Islands and the Atlantic Ocean. Many visit this town for its access to the national park, while others visit to explore the unique, walkable town.

Downtown Bar Harbor is a charming mix of Colonial Revival, Tudor, and Shingle-style commercial buildings. Memorable restaurants like The Chart Room and the Black Friar Inn and Pub are trademarks of the district. The quaint bed and breakfast is in the heart of downtown, perfect for a long weekend, and within walking distance of the main attractions.

Camden

The charming town of Camden is on Penobscot Bay, famous for its natural beauty and historic district. The High Street Historic District is a neighborhood filled with 19th-century architecture and grandeur and is available to tour. The neighborhood is a tangible tale of the town's architectural history that looks over the bay.

Notable attractions include the 1928-constructed Camden Public Library and Amphitheatre, a National Historic Landmark. Harbor Park, designed in the 1930s, retains its original paths leading to Penobscot Bay. You can book a room at the 1802 Camden Maine Stay Inn for a long weekend in a district pleasantly stuck in time.

Wiscasset

Wiscasset is considered one of the prettiest villages in the Pine Tree State. There are plenty of cultural attractions, historic homes, and museums to discover. The homes include 19th-century Federalist mansions like Castle Tucker and the Nickels-Sortwell House. The Lincoln County Museum and Old Jail is next door to the oldest operating courthouse in New England.

Wiscasset is also a foodie's dream and is famous for its lobster rolls. Local favorites include Sea Basket, Sprague's Lobster, and Sarah's Cafe. Visiting the Maine Tasting Center is a must. Here, you can sample many Maine culinary staples and take cooking classes to master the techniques for your home kitchen.

Stonington

Stonington is a traditional port town on Deer Isle with a friendly, inviting atmosphere and charming roads leading up from the harbor. The historic fishing village, lined with 19th-century buildings, is known for its commercial crab boats and art scene. Several galleries are located there, including Art by Katy and Jill Hoy.

No trip to a Maine port town is complete without a classic lobster dish. Stonington does not disappoint and offers notable restaurants like Aragosta and the Fin and Fern. There are also several cozy bed and breakfast inns. Booking a stay at the Inn on the Harbor or Pres du Port Bed and Breakfast provides an ideal lodging location near many sights.

Damariscotta

Damariscotta is a fun town to visit, especially in the Fall. It is famous for hosting the annual Pumpkinfest and Regatta, where 1,000-pound pumpkins are decorated in various ways. The festival also includes a pumpkin boat race and a parade. Other renowned festivals include the Pemequid Oyster Festival and Pirate Rendezvous.

The coastal village is surrounded by beautiful countryside; exploring it on foot is the best way to take in the scenery. It is also known for its cultural scene, which includes three live theaters and historic homes. The landmark structure is the Chapmanj-Hall House, built in 1754 and available to tour.

Kennebunkport

Historic Kennebunkport is a popular destination for a relaxing vacation. It is known for its beaches, Gooseneck and Arundel. The city is also famous for being the home of the George W. Bush compound. There are many historic homes, sites, and cultural attractions, like the Seashore Trolley Museum.

The museum is the first and largest Electric Railway museum in the world and features restored trolleys and a heritage railway. A landmark feature of Kennebunkport is the Wedding Cake House. The yellow two-story house was completed in 1825 and trimmed in elegant white trimming, a present from an imaginative sailor to his new bride. It is the most photographed house in Maine.

Ellsworth

Ellsworth is a cozy small town with a retro downtown featuring multi-colored brick storefronts. It is named after Founding Father Oliver Ellsworth and has many historic structures. The town claims 12 landmark buildings, including the Old Hancock County Sheriff's Home and Jail and City Hall. Another notable structure is the Grand Theatre.

The theater is an art deco centerpiece downtown, hosting many arts and entertainment venues. The Woodlawn Museum is a must-see cultural attraction. The interactive museum and estate tell the region's history through exhibits and artifacts. Ellsworth is also home to the interesting Telephone Museum, which makes for a fun visit.

Brunswick

Brunswick is a landmark town famous for its Maine State Music Theatre and other notable attractions. The theatre offers Broadway-like shows and is open year-round. Cultural attractions include the Skofield-Whittier House, built in the 1850s, and remains virtually untouched since it was last occupied in 1925.

Shopping is also a favorite pastime in Brunswick, primarily in the downtown area. The pedestrian-friendly shopping hub has brick sidewalks leading past bakeries, diners, and retail stores. Bohemian Coffee House, Lemon Block, and Wilbur's of Maine Chocolate Confections are just a few vendors. Gulf of Maine Books is housed in a clapboard New England building with a bay window and is an ideal way to spend an afternoon.

From historic villages to classic seaports, Maine has destinations for a long weekend. Bar Harbor's traditional architecture is ideal for retail therapy and salt air. Kennebunkport, filled with historical treasures, is also suitable for a relaxing weekend. Walking these towns with salt-tinged air and historic buildings is perfect for a long weekend.

Maine is beautiful year-round, depending on your travel preferences. These eight small towns and villages have much to offer guests, including charming bed and breakfasts where guests can sleep in and dive into the past. Some visitors come for the lobster, while others prefer sleepy villages. Maine has them all and is one of the best states for travelers to unwind.