15 Little Known New England Towns Everyone Must Visit At Least Once

Home to the United States Coast Guard Academy and the elite liberal arts school Connecticut College, this seaport town has whaling roots that can still be glimpsed in the beautiful downtown architecture. Today, visitors should be sure to spend some time in the 750-acre Connecticut College arboretum, which is home to a vast array of native flowers and endangered plants.

Go here for incredible fall foliage, quaint farms, rolling hills, and the crisp, clean air. Cheese lovers will appreciate a visit to Mountain Creamery, where they craft delicious dairy products out of local ingredients. Stopping by Billings Farm & Museum will give you taste of traditional Vermont farming and history.

Go here for the easy access to amazing skiing, and the world-class pancakes. Visitors to this beautiful New Hampshire town will be struck by the nature beauty and classic New England architecture, as well as the friendliness of the people. When you hear your stomach growl, head to Polly’s Pancake Parlor. There, you’ll find the most meltingly delicious pancakes ever, drenched in local maple syrup.

Norman Rockwell thought this place was so charming, that he based much of his artwork on scenes from around town. The historic Stockbridge Main Street looks much as it did when Rockwell painted it. James Taylor also sang about Stockbridge in his famous tune "Sweet Baby James." The Red Lion Inn has been catering to visitors since the 18th century, so your stay is sure to be one for the history books.

Rhode Islanders may be in the know about this picturesque island, but many don’t know that the little village on as Block Island is actually called New Shoreham. With no chain stores in sight (except a lone Ben and Jerry’s, because Ben and Jerry’s is as New England as the Kennedy family), this is a perfectly picturesque community that retains much of its 20th century charm. Even though Block Island may be a bit more high-profile than some other places on this list, New Shoreham doesn’t feel overdeveloped and its appeal as a small New England island hamlet is often overlooked in favor of spots on Martha’s Vineyard or Nantucket.

Go here for the absolutely incredible Gilded Age mansions. If you can only visit one, make it The Breakers – this "house" was modeled after Versailles and is by far the grandest of the bunch. The Newport Music Festival, held in early July, is also a great way to see this pretty coastal town and catch some world-class shows at the same time.

Go here for the incredible wine. Despite being known more for clam bakes and lobster rolls, New England can actually churn out some top-notch wines. Head to Sakonnet Vineyards for a leisurely stroll through 50 acres of picturesque grapevines and a taste of the best local vintages.

Located on Martha’s Vineyard, this place has to be the epitome of coastal New England living. Every street looks like a carefully constructed scene from the pages of Town & Country. Grey clapboard houses, bobbing white sailboats, penny candy shops, and flowering hydrangea bushes are just some of the quaint charms that Edgartown has to offer. Oh, and the beaches are world-class.

This place is a departure from the typical small New England town. Rather than tidy downtowns and clusters of old whaling homes, Rangeley offers plenty of wilderness, dramatic mountain views, and lots of peace and quiet. Gift shops and tourist attractions are pretty scarce, as the real draw here is the drama of the landscape and opportunity to hear yourself think.

Guilford isn’t as crowded with tourists as some other picturesque Connecticut towns, but it has plenty of charms that are all its own. Visitors can hike the various woodland trails surrounding the town, take a charted boat for a spin in the harbor, or sample some fruit straight from the bough at Bishop’s Orchards.

Go here for the history and plethora of wonderful B&B options. Hancock has one of those Main Streets where every single one of the buildings look like they could be on the National Register of Historic Places – and in this town, that’s actually the case. One of the original bells cast by Paul Revere still rings in Hancock’s downtown.

Cozy inns, old wooden homes, and a beautiful town green make Dorset the perfect place for a weekend getaway. Check out the gourmet deli in H.N. Williams Department Store, which is actually the town’s general store. It has a separate wine room for tastings and sipping, which definitely proves that Dorset is perfect blend of old-fashioned charm and modern class.

One of the oldest settlement in the nation, Castine is a gorgeous fishing village that feels like a postcard from the past. Visitors can learn about the area’s maritime history at the local Wilson Museum, or grab a deliciously fishy bite to eat Dennett’s Wharf.

This place is almost too quaint to stomach. Almost. The town actually burned to the ground in 1892, prompting the Main Street to be rebuilt entirely in brick. In 1947, the town held a lobster festival that asked visitors to pay only $1 for all-you-can-eat lobster. The festival was a huge success – too huge, apparently, as it was their first and last. Apparently the streets were covered in discarded lobster shells after the festival.