Fall foliage. Covered bridges. Cobblestone streets. Boat-filled harbors. Many images come to mind when one thinks of New England, a geographical region made up of Connecticut, Massachusetts, New Hampshire, Maine, Rhode Island, and Vermont. In addition to large cities like Hartford and Boston, the area is flooded with tiny towns full of history and charm. Below you’ll find the small towns worth visiting (for reasons you might not expect).
Best Town for Feeling Like You’re in a Rockwell Painting: Stockbridge, Massachusetts
Norman Rockwell, best known for his paintings capturing a certain idyllic Americana, was said to have taken much of his inspiration from the small New England town of Stockbridge. Not surprisingly, it’s home to the Norman Rockwell Museum, as well as many other worthwhile galleries, artists’ studios, museums, and historic sites. Visit the Red Lion Inn, which has been welcoming travelers with its kitsch and warmth since the the eighteenth century, or take a trip to nearby Tanglewood (the summer home of the Boston Symphony) for a picnic and a show.
Best Town for the Anti-Establishment: New Shoreham, Rhode Island
Aside from a lone Ben & Jerry’s, New Shoreham, located on Rhode Island’s Block Island, doesn’t have a single chain store or restaurant on it. At just under ten square miles, New Shoreham has the distinction of being the smallest town in the smallest state and is accessible only by air and ferry. It boasts over 17 miles of coastal beaches and 30 miles of picturesque walking trails. The assortment of shops, museums, restaurants, and tours available are sure to satisfy even the pickiest traveler.
Best Town for Embracing Your Inner Gilmore Girl: Washington, Connecticut
Though the town is named after George Washington himself and was founded in 1779, it’s also rumored to be the inspiration for everyone’s favorite fictional New England town: Stars Hollow. The gorgeous Mayflower Grace is said to be the inn the Independence (and later Dragonfly) Inn was based on. In between copious cups of coffee, make sure to visit the Institute for American Indian Studies, the Gunn Historical Museum, and the breathtaking Hollister House Garden.
Best Town for Recharging: Grafton, Vermont
A tiny town with fewer than 700 residents, Grafton is your quintessential tiny New England town. While quiet enough to rest and recharge, there’s plenty to keep you busy. Browse the art galleries lining the Grafton’s charming Main Street to get your creative juices flowing or visit the Grafton Ponds Outdoor Center for hiking, biking, canoeing, and more.
Best Town for Maritime Exploration: Mystic, Connecticut
While it might be best known as the setting for the Julia Roberts classic Mystic Pizza, Mystic, Connecticut, has more to offer than just pizza (though the pizza is worth trying). It’s also home to the nation’s largest maritime museum, the Mystic Seaport–whose collection includes the Charles W. Morgan, the world’s last remaining wooden whaling ship! Tourists can also stop by the Mystic Aquarium and visit penguins, beluga whales, and explore both indoor and outdoor attractions.