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Fun Places to Visit in the Northeast for the Holidays

Searching for something to do this holiday season? Look no further than this list of fun places to visit in the Northeast!

Lights twinkle over the Rink at Rockefeller Center.

(Photo: Sarah Hopkins)

Somehow, winter is both the best and worst season in the Northeast. On one hand, the temperatures are frigid and the road seems like it’s paved in black ice. On the other hand, there’s no better place to spend the holiday season (and there’s a good chance that you might get a white Christmas!) If you’re looking for fun places to visit in the Northeast, you’ll find the most amazing offerings around the holidays.

fun places to visit in the northeast

The ice rink at the Bryant Park Winter Village. (Photo: Sarah Hopkins)

New York City, NY

Let’s start at the very beginning, the epicenter of holiday cheer: Rockefeller Center. Rockefeller Center is full of amazing holiday sights and traditions, from the Christmas tree (which is 75 feet tall this year) to the magic of the Radio City Christmas Spectacular. You can also skate on one of the most famous ice rinks in the world, the Rink at Rockefeller Center. See the angel sculptures at the Channel Gardens and the fantastical windows and light displays at Saks Fifth Avenue. Right around the corner from Rockefeller Center is the idyllic Bryant Park Winter Village. The Bryant Park Winter Village consists of over 150 pop-up boutiques and eateries, surrounding a free-to-skate ice rink. It’s the best place to do your holiday shopping (and your holiday eating), and it’s one of the most fun places to visit in the Northeast for the holidays.

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fun places to visit in the northeast

Portland’s Monument Square during the holidays. (Photo: Corey Templeton / CC BY)

Portland, Maine

In Portland, Maine, there’s an 83% chance of a white Christmas, and this little city is full to bursting with holiday events. In Downtown Portland, which is extremely walkable, you can see colorful winter lights, part of an installation by artist Pandora LaCasse. If walking around is getting a little tiresome, try one of Portland’s free horse and wagon rides through Portland’s historic and festive downtown. You can also take a ride on the Maine Narrow Gauge Railroad Co.’s special Polar Express themed train rides. Maybe you’ll even wind up in the North Pole! At the Victoria Mansion, catch an immersive production of “The Nutcracker” performed by the Portland Ballet.

fun places to visit in the northeast

A covered bridge in Woodstock, Vermont. (Photo: Doug Kerr / CC BY)

Woodstock, Vt.

Forget upstate New York in the 60’s – Vermont is where it’s at. Woodstock is the quintessential Vermont town, complete with covered bridges, idyllic bed-and-breakfasts and beautiful ski slopes. In addition to all of this holiday fun is the local festival, Wassail Weekend. During Wassail Weekend, you can tour the historic homes of Woodstock, feast at the Woodstock Inn’s Wassail Celebration buffet and learn what an old New England Christmas was like at the Billings Farm. The crown jewel of Wassail Weekend is the Equestrian Parade, which features people dressed in colorful Christmas costumes on horseback. Don’t forget to bring some Woodstock maple syrup home with you!

fun things to do in the northeast

A window decorated for the Vintage Christmas candlelit walk. (Photo: Amy Meredith / CCBY)

Portsmouth, NH

For fun places to visit in the Northeast during the holidays, look no further than New Hampshire’s historic seaside city of Portsmouth. For over a decade, Portsmouth has celebrated a month-long festival called “Vintage Christmas.” You can hop on their free Christmas trolley and ride through the town to different events, like a live performance of “White Christmas,” a tasty gingerbread house contest, the outdoor skating rink at Puddle Dock Pond and a glowing holiday parade. To truly make it a Vintage Christmas, however, you must visit the Strawbery Banke Museum, which hosts a candlelit stroll through Portsmouth’s historic homes. The costumed performers waiting there will take you on a trip through holiday history. Before you leave, make sure to load up on all the presents you can carry. After all, New Hampshire doesn’t have any sales tax.

fun places to visit in the northeast

A vintage red truck takes its place during the “Stockbridge Main Street at Christmas” reenactment. (Photo: Frank Swift / CC BY)

Stockbridge, Mass. 

There’s nothing more quintessentially Northeastern than Norman Rockwell. And there’s nothing more “Norman Rockwell” than the holiday season. In Massachusetts, you can walk straight into Norman Rockwell’s “Stockbridge Main Street at Christmas (Home for Christmas).” The buildings of Stockbridge’s Main Street still look almost exactly as they did in the painting. Stockbridge even holds an annual celebration of the painting every December, where they meticulously re-create the scene that Rockwell painted, including the classic cars. Looking for lodging? You can stay in the Red Lion Inn from the painting! This snowy village is the epitome of the small town New England Christmas.

fun places to visit in the northeast

You can see the beautifully decorated interior of Gilded Age Newport mansions like The Breakers on a specially-themed Christmas tour. (Photo: SomeoneSaidFire / CC BY)

Newport, RI

Newport has always been one of the most fun places to visit in the Northeast, no matter the time of year. It’s no surprise that this town is chock-full of events tailored to the holiday season. There are tons of holiday events throughout December. You can see Santa Claus at the largest gingerbread lighthouse in New England, join in many Christmas concerts and carols, attend the 106th Annual Medieval Christmas Pageant, witness the tree lighting and so much more. There are also many Hanukkah events, like the Hanukkah Celebration at the Edward King House, with live music, performances, a menorah lighting and great traditional foods. To get an idea of the history of the holidays in Newport, go on the Holiday Lantern Walking Tour and catch a glimpse of Christmas past.

What’s your favorite place to spend the holiday season? Let us know in the comments below.

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