The 15 Most Charming Small Towns in New England

The first shots of the Revolutionary War were fired here. Add to that the fact that some of the most cherished American literary figures—Ralph Waldo Emerson, Louisa May Alcott and Henry David Thoreau—all lived (and felt inspired) here at one point. Note to self if you visit: Do not skip Walden Pond.

Where to stay: If you want everything within walking distance (for the most part), the Colonial Inn is your best bet. Originally built in 1716, it’s been properly modernized, but allows you to fully immerse yourself in the historic nature of the town. (There are even rumors that some of the rooms are haunted.)

OK, so you have to take a short ferry ride to visit this super-cute Martha’s Vineyard town, but it’s worth the trip to see the old whaling port, bustling with old-school Americana and celebrity sightings. (We’re talking about you, Barack Obama.)

Where to stay: It’s a toss-up between the Harbor View Hotel (which was recently renovated and comes with views of the Edgartown lighthouse) and the Christopher (tucked away on a quiet street, but with a beach-meets-Victorian vibe). Each are located right in the heart of downtown.

It’s no surprise that most of the buildings in this tiny (and quintessential) New England town—founded in 1787—are on the National Register of Historic Places. Located in the Green Mountains, the town boasts just about 3,000 residents, plus plenty of things to do and see, from perusing the Woodstock Farmers’ Market to catching live music at the Woodstock Town Hall Theatre.

Where to stay: While the town itself has much to explore, the luxurious Woodstock Inn & Resort comes fully loaded with four restaurants, a spa and golf course, not to mention stunning accommodations that are both quaint and posh.

Um, Norman Rockwell used this town in the Berkshires as inspiration for his work. That is all.

Where to stay: The Red Lion Inn—located right in the heart of Stockbridge—is full of antiques and old-fashioned charm or you could try staying one town over in Lenox at the ultra-charming 11-room Gateways Inn.

The vibes are chill in this seaside town—so chill that you could actually commit to getting around without a car. (The East Bay Bike Path kicks off here and you can ride it all the way to Providence.)

Where to stay: A Colonial federal-style home that has been converted into a bed-and-breakfast, the William’s Grant Inn is located on a tree-lined street and within walking distance to all of Bristol’s restaurants, shops and museums.

Sure, it’s home to the infamous private school (Phillips Exeter Academy), but it’s also home to an assortment of mom-and-pop shops, restaurants, art galleries and some of the best foliage you’ll ever Instagram.

Where to stay: The Exeter Inn is quintessential New England—think stately trees, a romantic courtyard, elegant architecture—and Phillips Exeter is practically in its backyard. (The exploration begins now.)

This town offers ocean views and artisanal (and adorable) ice-cream shops. Plus, you’re a hop, skip and a jump hike away from Acadia National Park.

Where to stay: It’s called the Saltair Inn for a reason—this waterfront property takes its cues from the Frenchman Bay it looks out at. Open all four seasons, nab a room (there are only eight) before they’re all booked up.

Yes, the mansions—like the Breakers—are epic. But so are the sunsets, the coastal walkways and all the charming (regular-sized) homes.

Where to stay: Located on the edge of Narragansett Bay, the Vanderbilt combines gilded age luxury and glamour with a relaxed energy and plenty of charm. (Did we mention there’s a seaside pool, too?)

Located on the Southeastern tip of Massachusetts’s bent “elbow,” Chatham is a vibrant part of Cape Cod—home to beautiful beaches, but also plenty of culture, from the Chatham Shark Center, which focuses predominantly on the Great White, to the Monomoy National Wildlife Refuge, a nesting and feeding habitat for migratory birds.

Where to stay: Check out the Chatham Bars Inn, which features it’s own private quarter-mile beach and on-site farm in addition to a spa, pool, tennis and golf. (Plus, it’s pretty hard to beat these views.)

Right on the edge of Penobscot Bay, this postcard-perfect seaport has it all—mountain views, delicious seafood nearby and (made in Maine) wine.

Where to stay: Fresh off a renovation, the Captain Swift Inn is a boutique hotel with nine unique guest rooms—some even have private decks—and a candlelight breakfast experience that is not to be missed.

There are approximately 500 year-round residents in this quaint little spot, nestled on the edge of the beautiful White Mountains. But a visit to this small town will make a big impact. Tip: The local country store makes its own cheddar from scratch, so don’t miss out.

Where to stay: About the White Mountains...the Sunset Hill House has sweeping views of them, not to mention access to the world’s oldest golf course (guests can play nine holes) in addition to pristine gardens and a pool.

Home to the pizza pie made famous by Julia Roberts (#TBT), this town’s reputation extends well beyond that. Go for the Mystic Museum of Art and the Mystic Aquarium (home to beluga whales!); stay for the water views. (And, OK, a slice of that delicious pizza.)

Where to stay: At the Whaler’s Inn, a boutique hotel located in the heart of a bustling maritime village, guests have the option to choose from five adjacent properties—from the historic 1865 House to the adults-only Hoxie House—in which to stay.

It’s frequently referred to as the prettiest town in Maine, but Wiscasset is also known for it’s old-fashioned charm. Case in point: the Maine Heritage Village, which is chock-full of stores featuring Maine-made products. But there’s also the food (ahem, Red’s Eats earned the accolade of best lobster roll in the state) and there’s also plenty of architectural landmarks worth checking out. (Psst...the town is also home to the world’s smallest church, per the Guinness Book of World Records.)

Where to stay: Just six miles outside Wiscasset, the Newcastle Inn earns rave reviews for its daily home-cooked breakfast and uninterrupted views of the Damariscotta River. (Just pull up an Adirondack chair.)

It’s the Hamptons of Maine if you will—a small yet ritzy town beloved by presidents and celebrities alike. Dock Square is the focal point. There, you’ll find al fresco dining hot spots mixed in with shops, art galleries and more. If the sea and surf is what you’re looking for, Goose Rocks Beach is a can’t-miss with a three-mile stretch where you can just meander.

Where to stay: Choose from any one of the nine properties within the Kennebunkport Resort Collection (say, the Grand Hotel or the Tides Beach Club) and you’ll experience first-rate hospitality and easy access to the best of the area.

It’s what the fictional town of Stars Hollow from Gilmore Girls is based on. Enough said.

Where to stay: The Mayflower Inn & Spa feels more like a retreat than a hotel. Expect four-poster beds and an English countryside vibe. And definitely do yourself a favor and leave enough time for a glass of wine on the porch.