The 40 Prettiest Winter Towns in America: Seven are in New England and Just a Drive Away!

Listen, who wants to get on plane during the winter? (If you do, there are some beautiful places on this list to visit.)

But if you want a winter wonderland just a drive away, these are the most picturesque holiday towns in New England, according to Country Living magazine.

I can imagine cozying up in front of a fire in any of these towns, sipping on some cocoa and doing some holiday shopping.

Two of the towns are in Massachusetts. Sure, you have to take a ferry to get to Nantucket. Who cares?

The Christmas Stroll is a bevy of Nantucket reds, money and tinsel! (Never been, but it’s on my bucket list.)

As for the sleeper hit Sandwich, sure it’s fabulous in the summer, but who knew it was a go-to destination in winter?

Truth be told, all of the Cape is amazing during the colder months. But be warned, lots of places are closed for the season. If you’re looking for quiet, though, it’s the place to be.

Check out these perfect New England winter towns where you can cozy up with the ones you love!

• 7. Woodstock, Vermont

  “With covered bridges, skiing, and the holiday-themed Wassail Weekend celebration, Woodstock is a bucolic town with a traditional American Main Street—and it looks particularly lovely when it’s covered in snow,” according to Country Living.

  View this post on Instagram

  A post shared by Woodstock Inn & Resort (@woodstock.inn)

• 6. Sandwich, Massachusetts

  “Cape Cod may have a stronger rep as a beach destination, but it’s gorgeous in the wintertime! The town of Sandwich is one of the oldest on the Cape, incorporated in 1639, and its scenic boardwalk is a must-visit, no matter the season,” Country Living said.

  View this post on Instagram

  A post shared by Salty Girl Studios (@saltygirlstudios)

   

• 5. Mystic, Connecticut

  “When Santa comes to Mystic, he travels by tugboat! His arrival is followed by another Mystic tradition: the Holiday Lighted Boat Parade, which celebrates the town’s nautical heritage,” according to Country Living’s list. 

  View this post on Instagram

  A post shared by This is Mystic, CT (@thisismystic)

• 4. Nantucket, Massachusetts

  “For some 50 years, the summer town of Nantucket has hosted an annual Christmas Stroll, during which carolers sing, Santa pays a visit, and revelers walk about town with jolly spirits (there may be some mulled wine involved for adults). A season of essentially zero crowds means wide open beaches for additional strolls and off-season pricing on accommodations. Win-win!” Country Living reported. 

  View this post on Instagram

  A post shared by Endeavor Sailing Excursions (@endeavorsailing)

• 3. Littleton, NH

  Country Living says “Littleton is surrounded by skiing, but there’s plenty to do in town too. The quaint spot is home to the world’s longest candy counter, as certified by the Guinness Book of World Records (it’s 112 feet long!), and a variety of funky boutiques. Stop by the Littleton Diner for brunch, then mosey over to the Schilling Beer Co. for local brews.”

  View this post on Instagram

  A post shared by Littleton Main Street (@littletonmainstreet)

   

• 2. Portsmouth, New Hampshire

  “Established in 1653, Portsmouth is a quintessential New England port town located about an hour outside of Boston. In the winter, enjoy sports like fat-tire biking and ice-skating, followed by après- ski-style drinks in one of Portsmouth’s many restaurants and bars,” Country Living said.

  View this post on Instagram

  A post shared by Capturing Portsmouth (@capturingportsmouth)

   

• 1. Bar Harbor, Maine

  “As cute and charming as Bar Harbor is, it gets busy in the summer. You can take advantage of the cleared-out crowds in the winter, both in town—where you can, and should, enjoy some chowder to warm yourself up—and in nearby Acadia National Park,” Country Living reported.

  View this post on Instagram

  A post shared by Bar Harbor, Maine (@visitbarharbor)

Sign me up for the HOT 96.9 email newsletter!

Stay connected with the hottest celebrity and music news, plus exclusive prizes, trips, and more!

First Name *

Last Name

Email *

Subscribe

By clicking "Subscribe" I agree to the website's terms of Service and Privacy Policy. I understand I can unsubscribe at any time.