Northeast Vacations: The 9 Cutest Towns for Your Trip

By Kacey Bradley
December 18, 2019
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Tiny cottages with smoke puffing from their chimneys. Glassy water crashing into rocky coastlines. Fishermen pulling up cages full of fresh lobster. We all have an image of what New England looks like, and most of our daydreams of the Northeast have roots in reality. Now, you want to see this picturesque pocket of the country for yourself. Here are nine towns to visit for the quaintest, coziest version of the Northeastern U.S. 

1. Grafton, Vt.

Only 600 people call Grafton their home year-round, but that's not a reflection on the place's exorbitant amount of charm. Instead, you'll find sheep grazing in pastures, cute covered bridges and all the coziness you could want from family farms and inns. On that note, be sure to check out the Grafton Village Cheese Co., where you can sample the town's finest yields, including truffle cheddar and sheep gouda. 

2. Bar Harbor, Maine

Outdoor enthusiasts will love a Northeastern adventure in Bar Harbor. Here, you'll find Cadillac Mountain, the eastern seaboard's highest point, as well as the stunning Acadia National Park. Explore the highlights for a weekend, or stay longer for a well-rounded experience of this gem of a town. You'll have fresh seafood and plenty of fare from Bar Harbor's famously tasty independent restaurants to sustain you through it all. 

3. Stockbridge, Mass.

Norman Rockwell once lived here, which hints at just how perfectly picturesque Stockbridge is. This cute town sits in the Massachusetts Berkshires, which have become a go-to escape for city dwellers in both Boston and NYC. You can sneak away here, too, and enjoy all of its New England charms, which include a historic main street, country stores and an independent coffee roaster. 

4. Bristol, R.I.

Bristol could be the perfect place for a July 4 vacation, especially because it has a reputation for being the most patriotic town in the nation. At that time, you can take in the iconic soapbox races, parades and concerts that celebrate our country's birthday. Of course, visiting Bristol at another time of the year won't disappoint, either. Check out the Blithewold Mansion, Gardens and Arboretum, a stunning building that also set the scene in The Great Gatsby, starring Robert Redford and Mia Farrow. 

5. Portland, Maine

The Pacific Northwest's Portland gets all the attention, but we'd argue that the Northeastern contingent has all the charm. Portland's an especially big draw in fall, when its leaves change colors in a stunning display you could only find in New England. To that end, Portland's known for its fabulous food and beverage scene. Nosh on fresh lobster, then wash it all down with a local craft beer. Yum. 

6. Mystic, Conn. 

Thanks to the 1988 film Mystic Pizza starring Julia Roberts, plenty of people know about this Northeastern destination. Even if the place — and its iconic pizzeria — have become a touristy destination, it's still a worthy consideration for your New England trip. For one thing, the village has its traditional, old-school main street. You can stroll down by the water, too, and grab a bite at any number of restaurants that take advantage of the view. You'll also find plenty of adorable bed-and-breakfasts, as well as an aquarium, great for little travelers who have tagged along on the journey.  

7. Hudson, N.Y.

Yes, you can find quaint charm in New York — just step away from the city. Upstate's Hudson was once a resort town, and now it's home to a thriving art scene. You can check that out or see all the natural beauty that the area has to offer. Not only can you hike your way through Taconic State Park, but you can take a short drive over the border into Massachusetts to see the stunning Bash Bish Falls. 

8. Frenchtown, N.J.

Size doesn't matter when it comes to this tiny gem in New Jersey. It's certainly on the smaller side, but Frenchtown has plenty of boutiques and tasty restaurants to fill out your weekend getaway. As such, it might be a great place to escape to when it's cold or otherwise dreary outside. Skip from shop to shop, eat at a one-of-a-kind restaurant and avoid the bad weather amid some serious charm. 

9. Nantucket Island, Mass.

You can't write a list of the Northeast's best destinations without including Nantucket Island. There's a reason so many people vacation here — including the Obamas, who purchased a sprawling estate on the island. Rather than finding yourself on a beach brightened by strip malls and commercial outposts, you'll find a quaint, coastal destination with independent shops and restaurants. You can hop on a bike or boat to explore the stunning landscape. And you can tuck in at night in one of the many charming bed-and-breakfasts that make Nantucket such an iconic destination for visitors in the summertime and beyond. 

Head Northeast

You now have nine great options for your trip into the Northeast. Where will you go? No matter where you end up, you're sure to find all of the warmth and charm you seek from this notoriously adorable region. So, get going and enjoy every minute. 



Kacey Bradley is the blogger behind The Drifter Collective, an eclectic lifestyle blog that expresses various forms of style through the influence of culture and the world around us. Along with writing for her blog, she has written for sites like U.S. News, SUCCESS, Guides for Brides, Hotel Online and more!

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