6 Quirky Small Towns to Visit in New England

For history buffs, New England offers plenty to explore of the nation’s colonial past. This northeastern corner of the United States — comprising the states of Connecticut, Maine, Massachusetts, New Hampshire, Massachusetts, Rhode Island, and Vermont — is also filled with charming small towns amid forested mountains and scenic coastal areas. If you’re looking to get off the beaten path on your next adventure in the region, here are six of New England’s quirkiest and most charming small towns to visit.

Woodstock, Vermont

Woodstock’s artsy vibe and buzzing creative atmosphere become apparent as soon as you step foot in the town of roughly 3,000 people in central Vermont. It’s not your imagination: Woodstock was founded by artisans, entrepreneurs, and craftsmen who settled here in 1786 and made it one of the largest towns in Vermont at the time. Today, the artistic culture and entrepreneurial spirit can be found in the quirky boutiques, farm-to-table restaurants, and unique creations and handicrafts sold by local makers. 

A number of attractions are clustered near the town center, known as the Green. From here, you can easily walk between the iconic Middle Covered Bridge, the historic Town Hall Theater (be sure to catch a show if you have time), the 19th-century Norman Williams Public Library, and a host of charming cafes and shops. 

Provincetown, Massachusetts

Sitting at the northernmost tip of Cape Cod, Provincetown draws a more laid-back crowd than much of the peninsula. A picturesque coastal destination with a free and easy-going attitude, Provincetown appeals to artists, creatives, and, in particular, the LGBTQ+ community. The town also has a high percentage of Portuguese immigrants, expanding the cultural depth of the eclectic community. 

P’town (as it’s affectionately known) is also where stars like Al Pacino, Bette Davis, and Angela Lansbury launched their acting careers. Some, like Al Pacino, got their start at the historic Gifford House, a historic inn that once hosted an experimental theater. The same inn has also welcomed several Presidents, including Ulysses S. Grant, Theodore Roosevelt, and William Howard Taft. 

Mystic, Connecticut

The village of Mystic is home to under 5,000 people, but what the seafaring community lacks in size it makes up for in rich history. Since the 1600s, Mystic had been a hub for shipbuilding. At the height of the American maritime industry, between 1784 and 1919, the village produced around 600 boats. Visitors can learn the prosperous history at the Mystic Seaport Museum — the largest maritime museum in the country — and see the only wooden whaling vessel still in existence, the Charles W. Morgan. 

Movie fans may also recognize Mystic as the inspiration for Mystic Pizza, the 1988 movie that put Julia Roberts on the map. The real-life Mystic Pizza refused to shut down their business for filming, so much of the movie’s scenes were filmed nearby and in a staged pizza parlor. The shop later renovated its appearance to look more like the movie set version and has benefitted from a surge in popularity ever since the film’s release. 

Castine, Maine

Castine — a beautiful hamlet in mid-coast Maine — is one of the oldest communities in North America. Continuously inhabited since the early 1600s, Castine boasts a diverse heritage. The French, Dutch, British, and Etchemin Native Americans all battled for control of this prosperous port city. Telltale signs of Castine’s storied history are still scattered around town — including Fort George (built by the British in 1779), Fort Madison (constructed by the U.S. Army in 1808), Fort Pentagoet (built by the French in the 1630s), and the historic waterfront. 

A port city at its core, Castine boomed in the 1800s before the Civil War and hosted hundreds of vessels in its advantageously deep harbor. In fact, due to the fishing, salt, and shipbuilding industries, Castine was once one of the wealthiest cities in the U.S. on a per capita basis. Proof of this is seen today in the beautifully restored Georgian mansions scattered around town.

Burlington, Vermont

This picturesque city on Lake Champlain is known for more than just its postcard-perfect appearance — it’s also the birthplace of the band Phish and Ben & Jerry’s ice cream. Burlington doubles as a funky college town surrounded by quintessential New England nature. Like many New England towns, Burlington is proud of its local makers and creators. Visitors can purchase unique souvenirs like the state’s famous maple syrup, antique gems at the Vintage Inspired Marketplace, local ciders and brews, and of course, a Vermont-made flannel. 

If that’s not enough to keep you busy, you can always check out attractions such as the World’s Tallest Filing Cabinet or the interactive art installation known as the Burlington Earth Clock. The latter’s location along the Burlington Bike Path doubles as an impressive viewpoint over Lake Champlain. 

Conway, New Hampshire

Conway is a scenic and historic town of around 10,000 people in eastern New Hampshire. The town attracts a mix of tourists, some who come to take advantage of its proximity to the region’s famous White Mountain National Forest. Others are drawn to the quaint vibes and family-friendly activities. Conway is divided into five villages, the most well-known of which is North Conway. Serving as the gateway to the White Mountains, a range that covers roughly a quarter of New Hampshire, the village is a hub for avid hikers eager to tick 4,000-plus-footers off their bucket lists, as well as the tallest mountain in the northeast, Mount Washington. 

Less keen hikers might choose to experience New England nature in a more laid-back manner by riding the Conway Scenic Railroad or taking a dip at Echo Lake State Park. North Conway is also a shopping hub, offering several tax-free outlets, as well as independent coffee shops, local cafes, and a famous general store. If the family’s in tow, a trip to the Story Land might be on the list, too.