The 15 Most Charming Small Towns in New England

• Why We Love It: It’s quiet and historic, but also bustling
• Things to Do: Shopping, exploring and touring, Walden Pond
• Where to Stay: The Colonial Inn (from $196/night); North Bridge Inn (from $180/night)

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. (I grew up in the area and can attest: The nature preserve is stunning, picturesque and a sanctuary, no matter the season.) Ditto shopping in downtown Concord. (A sandwich from the Concord Cheese Shop is a must-try.)

• Why We Love It: A nautical setting but with a super-fun nightlife
• Things to Do: Eating, beach trips, shopping and celeb spotting
• Where to Stay: The Christopher (starts at $544/night); Harbor View Hotel (starts at $240/night); Edgartown Home (sleeps 6; starts at $332/night)

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.) Go for the fresh seafood, stay for the pristine beaches, all framed by colorful cliffs, according to our editorial team. The Christopher is located right at the center of it all, making it an easy walk to dozens of Edgartown shops and restaurants. A must-try spot? The Port Hunter, known for its cuisine and cocktails, but also its live music on Friday nights.

• Why We Love It: It’s historic, but also home to a thriving arts community
• Things to Do: Eating, shopping, antiquing, Woodstock Farmers’ Market
• Where to Stay: The Village Inn of Woodstock (starts at $295/night); The Woodstock Inn (starts at $326/night); The Looking Glass (sleeps 2/starts at $303/night)

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, not to mention a thriving arts community. (If you leave with a trunk full of original art—or inspired to pick up the hobby yourself—don’t be surprised.) But for its quiet and peaceful vibe, there’s still plenty of things to see and do, from perusing the Woodstock Farmers’ Market to catching live music at the Woodstock Town Hall Theatre. You’ll also want to make time for a stop at the Long Trail Brewing Company for a VT IPA.

• Why We Love It: It’s steeped in history, but also the perfect fresh air escape
• Things to Do: Dining, shopping, Norman Rockwell Museum
• Where to Stay: The Red Lion Inn (starts at $190/night); The Inn at Stockbridge (starts at $314/night); Cabin at Stockbridge (sleeps 6; $175/night)

Both Norman Rockwell and Dorinda Medley (of Real Housewives fame) would attest: This rural town in the Berkshires is worth visiting. It’s true: Rockwell famously used this Western Massachusetts town as inspiration for his work—and I can understand why. My own drives—windows down—around the hilly and scenic terrain make it the kind of place where you want to cue up a classical playlist and relax. While there, you’ll want to make a point to stop by the Norman Rockwell Museum (of course), but also Naumkeag, a botanic garden and Gilded Mansion, too.

• Why We Love It: A picturesque spot with plenty of mom-and-pop shops
• Things to Do: Eating, drinking, shopping, East Bay Bike Path
• Where to Stay: Bristol Harbor Inn (starts at $127/night); William’s Grant Inn B&B (starts at $185/night); Bristol Cottage (sleeps 6; starts at $278/night)

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, FYI.) There’s more: The town is chock full of mom-and-pop shops and cute cafés and restaurants (Le Central is a dream for brunch), adding to the leisurely atmosphere. Other activities worth prioritizing? The Blithewood Manor and Gardens, a 45-room estate that features grand views of Narragansett Bay, not to mention a range of special events. (A talk about the Blithewood Costume collection? Sign us up.)

• Why We Love It: The historic town is home to Phillips Exeter, but also plenty of art
• Things to Do: Eating, dining, shopping, art gallery hopping
• Where to Stay: The Exeter Inn (starts at $139/night); The Word Barn (starts at $150/night)

Sure, it’s home to the infamous private school (Phillips Exeter Academy), but it’s also home to an assortment of unique shops, restaurants, art galleries and some of the best foliage you’ll ever Instagram. The Seacoast Science Center is a can’t-miss, but so is a walk along part of the Phillips Exeter trail (the 30-mile loop connects a handful of New Hampshire towns and ends at the posh prep school). 

• Why We Love It: It’s the gateway to Acadia National Park
• Things to Do: Hiking, eating, Acadia National Park
• Where to Stay: Ivy Manor Inn (starts at $122/night); The Bar Harbor Inn (starts at $209/night); New Modern Cabin (sleeps 2; starts at $150/night)

Complete with ocean views and artisanal ice-cream shops, Bar Harbor is a seaside village—and gateway to Acadia National Park—that offers shopping, fine dining and stunning water views at nearly every turn. If you’re going, a hike through Acadia should be top of the list; specifically, Cadillac Mountain, which features spectacular views over to the bay and Cranberry Islands. (If you’re an early bird, the sunrise view in particular can’t be beat.) The Shore Path is another must-do. The scenic and leisurely hike starts at the town pier and runs along the easter shore of Mount Desert Island—no hiking boots required.

• Why We Love It: The food scene is impressive; so are the water views
• Things to Do: Shopping, touring the mansions, boat tours of Newport Harbor
• Where to Stay: The Brenton Hotel (starting at $200/night); Newport Marriott (starting at $246/night); Pelham Court (sleeps 4; starting at $171/night); Island House Newport (starting at $195/night)

Yes, the mansions—like the Breakers—are epic. But so are the sunsets, the coastal walkways (leave time for the Cliff Walk) and all the charming (regular-sized) homes. On a recent visit, I was blown away by the range of things to do, from the Sailing Museum to the Tennis Hall of Fame to simply popping into St. Mary’s Roman Catholic Church, the iconic chapel where John F. Kennedy married Jackie. Oh la la. To top it all off, the culinary scene has exploded—Bar ‘Cino and Mother Pizzeria are not to be missed.

• Why We Love It: It’s as picturesque as it is coastal
• Things to Do: Beach trips, fine dining, Chatham Shark Center
• Where to Stay: Chatham Bars Inn ($404/night); Greyfinch Chatham Inn ($219/night); Slate House (sleeps 9; starts at $365/night)

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. Based on my own experience visiting, I’d say this is a town you want to experience in the summer, when the al fresco dining scene is bustling and the hydrangeas are in peak bloom.

• Why We Love It: Mountains meet the sea in this idyllic town
• Things to Do: Hiking, dining, shopping, exploring
• Where to Stay: Norumbega Inn (from $279/night); Grand Harbor Inn (from $249/night), Camden Village Tree Cottage (sleeps 2; from $160/night)

Right on the edge of Penobscot Bay, this postcard-perfect seaport has it all—mountain views, delicious seafood nearby and (made in Maine) wine. Spend a morning kayaking in Rockport Harbor, an afternoon hiking out to Maiden’s Cliff, you can even nab a spot on a local schooner for a sunset sail. When all is said and done, just be sure to save room for ice cream—River Ducks and Camden Cone are both worth a stop.

• Why We Love It: Breathtaking mountain views and summers scented by lupine
• Things to Do: Hiking, leaf peeping, dining
• Where to Stay: Franconia Inn (from $163/night); The Sunset Hill House (from $95/night); The Honeypot Cabin (sleeps 9, from $323/night)

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. Many flock to the area in early summer for a glimpse of the colorful lupine, which covers the hillsides at this time. The annual Lupine Market is also a must-see. The local country store is also worth stopping by—they make they’re own cheddar from scratch, so don’t miss out.

• Why We Love It: The town’s pop culture connection, but also the aquarium
• Things to Do: Shopping, eating, the Mystic Aquarium
• Where to Stay: The Whaler’s Inn (from $204/night); Hyatt Place Mystic (from $111/night); Harbor View Landing House Boat (sleeps 2, from $499/night)

Home to the pizza pie made famous by Julia Roberts, this town’s reputation extends well beyond that. I repeatedly make a point of detouring to the Mystic Aquarium (home to beluga whales, but also a stunning and expansive indoor/outdoor experience). The Mystic Museum of Art is also worth a stop, but that pizza slice really is worth it (so is breakfast at the Mystic Diner).

• Why We Love It: It’s as charming as it is quiet
• Things to Do: Dining, shopping, exploring, Red’s Eats
• Where to Stay: Charming Sea Cloud Cottage (sleeps 4; from $183/night); Cottage with Spectacular View (sleeps 6, from $153/night); Tiny A-Frame Home (sleeps 3, from $222/night)

It’s frequently referred to as the prettiest town in Maine, but Wiscasset is also known for its old-fashioned charm. Case in point: A walk along main street, which is chock-full of stores featuring Maine-made products. (We’re partial to Rock Paper Scissors, but also Moulinette for cute kids items.) There’s also a vibrant food scene (ahem, Red’s Eats earned the accolade of best lobster roll in the state) and plenty of architectural landmarks worth checking out (for example, the world’s smallest church, per the Guinness Book of World Records).

• Why We Love It: A tiny Maine town where luxe meets low-key
• Things to Do: Beach trips, fine dining, art gallery hopping
• Where to Stay: Yachtsman Hotel & Marina Club (from $479/night); Nonantum Resort (from $483/night); Modern, Pet-Friendly Cabin (sleeps 4, from $663/night)

It’s the Hamptons of Maine if you will—a small yet ritzy town beloved by presidents and celebrities ranging from Patrick Dempsey to George H.W. Bush. 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.

• Why We Love It: It’s as darling as it’s on-screen alter-ego
• Things to Do: Hiking, dining, shopping, Hidden Valley Preserve
• Where to Stay: The Mayflower Inn & Spa (from $1,224/night); The Abner Hotel (from $444/night); Country Hideaway Cottage (sleeps 4, from $141/night)

It’s what the fictional town of Stars Hollow from Gilmore Girls is based on. In actuality, it feels as charming as it’s on-screen depiction. Complete with one-of-a-kind shops (we’re talking to you, Hickory Stick Book Shop) as well as stunning hikes (like through the Hidden Valley Preserve), there’s plenty to eat, drink and do while in town. And if relaxation is your number one plan, don’t miss a day at the Mayflower Inn & Spa, a true sanctuary where you can indulge in everything from a facial to yoga—followed up with a glass of wine.