Tranquil scene at Commercial Street in Provincetown, Mass. Editorial credit: Rolf_52 /

6 Picturesque Small Towns in New England for a Weekend Retreat

The New England region comprises six northeastern US states: Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. The geography is diverse, with Canada to the north, the Atlantic Ocean to the east, Long Island Sound to the south, and New York to the west. Small towns are the fabric of New England and represent the industrious, hard-working people that call the region home. 

 The Colonial architecture of the buildings and the maritime history embody the spirit of New England. Here are six picturesque New England towns perfect for a weekend retreat.

Woodstock, Vermont

Middle Covered Bridge in Woodstock, Vermont.
Middle Covered Bridge in Woodstock, Vermont.

Woodstock, Vermont, was chartered in 1761, and many buildings are on the National Register of Historic Places. Calvin Coolidge's home and the Norman Williams Public Library are two such historic buildings. Another landmark is the Middle Covered Bridge, spanning the Ottauquechee River in the heart of town.

The downtown area is one of the prettiest in New England, and it centers around The Green, Woodstock's Central Park. Notable shops include Yankee Bookshop and Woody's Mercantile. The Woodstock Inn and Resort is an upscale hotel on Main Street that provides an elegant stay for your weekend and easy access to downtown. 

Provincetown, Massachusetts

Cape Cod Provincetown beach Massachusetts, USA.
Cape Cod Provincetown Beach, Massachusetts, USA.

Provincetown, Massachusetts, is a seaside town that was the first landing for the Mayflower in 1620. It is known for its artistic atmosphere and is a foodie's haven. "Ptown" has a vibrant cultural scene, and there are over 50 art galleries, including the Adam Peck Gallery, the Bakker Gallery, and the Schoolhouse Gallery. 

Provincetown also has many hiking and bicycle trails and several bike rental shops downtown. Commercial Street is the defacto main street here and the hub of the entertainment and food district. Great locations include restaurants like the Portugese Bakery and multiple shops and museums like the Cortile Museum. 

Mystic, Connecticut

Mystic Seaport, outdoor recreated 19th century village and educational maritime museum in Mystic, Connecticut. Editorial credit: Faina Gurevich /
Mystic Seaport outdoor recreated 19th-century village and educational maritime museum in Mystic, Connecticut. Editorial credit: Faina Gurevich /

Mystic, Connecticut, has an impressive maritime history, with 600 ships being built here over a 135-year period. It is on the Mystic River, which grants the town access to the Atlantic Ocean. The Mystic Aquarium & Institute for Exploration is in Mystic and is a popular tourist destination.

Besides the maritime history and marine rehabilitation center, Mystic is known for its lively downtown region. If you want to spend the weekend in the middle of downtown, book a room at the Steamboat Inn. Eleven rooms have water views and are equipped with a gas fireplace for seasonal weather. 

Exeter, New Hampshire

Historic town center of Exeter, New Hampshire. Editorial credit: Wangkun Jia /
The historic town center of Exeter, New Hampshire. Editorial credit: Wangkun Jia /

Exeter is a historic maritime port dating back to 1638. The Exeter Historical Society has done a great job preserving the local history through record preservation and historical material. The Gilman Garrison House on Water Street was built in 1709 and has been preserved through the Historical Society.

Exeter played a key role in American history and the American Revolution. History buffs should check out the American Independence Museum to discover the stories about the men who contributed to American independence. The Exeter Inn, in the heart of town, is a two-story brick boutique hotel that captures an authentic New England experience. 

Bar Harbor, Maine

Aerial view of Bar Harbor, Maine.
Aerial view of Bar Harbor, Maine

Bar Harbor is another historic seaport in Maine's Frenchman Bay. The town was founded in 1796 and had commercial fishing, lumbering, and shipbuilding industries.  It is also the gateway to Acadia National Forest and draws outdoor enthusiasts year-round for the virtually endless outdoor activities.

There is also plenty to see downtown, where the buildings blend Shingle and Victorian Gothic architecture for a classic New England aesthetic. A stroll down Main Street and the Shore Path is a must. There are guided walking tours that allow you to explore the various shops while learning about the vast history of Bar Harbor. Book a room at the Acadia Hotel downtown to complete your weekend stay. The rooms are affordable, and the location puts you in the center of downtown. 

Wickford Village, Rhode Island

Entrance of Wickford Harbor in the Narragansett Bay.
Entrance of Wickford Harbor in the Narragansett Bay.

Wickford Village is a historic town with picturesque roads and historic homes with Federal and Colonial architecture. You can take a guided carriage ride down Main Street to soak in the village's views and history. The Historic District was a trading post in the 17th century, and shops and galleries can still be found here.

Summer is a terrific time to visit when, on select Fridays, the harbor is lit up, businesses stay open later, and food trucks arrive to fuel the party. Of course, there are amazing dining options as well. Today, Wickford is a popular destination for shopping with popular stores like the Village Faire, the Green River Silver Company, and many more antique shops and galleries.

New England is a fascinating place. The historic seaports and towns helped shape America, and today, they still preserve the classic New England aesthetic and vibe. Provincetown is where the first Pilgrims made landfall, while Bar Harbor played a pivotal role in developing the modern shipping industry in Maine. If you want a weekend getaway, these six towns fit the bill for outdoor activities, historical significance, and leisurely fun.

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