9 Ways to Have a Charming Stockbridge MA Christmas


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When you think of charming Christmas towns in New England, what sort of scene do you imagine? Chances are, it’s like something out of a Norman Rockwell painting, perhaps even the one depicting a Stockbridge MA Christmas?

That’s right, that quintessential small-town covered in snow with the wreaths and the garlands and the warm, cozy lights, was modeled after the actual town of Stockbridge MA at Christmas! If you’re looking to experience a little of that wholesome, small-town New England Christmas charm for yourself, head to the Berkshires for a good, old-fashioned Stockbridge MA Christmas!

Christmas Shop at the Berkshire Botanical Garden Holiday Marketplace

Handcrafted Christmas Wreath being held by woman in white sweater

Looking for some unique and interesting Christmas gifts to fill the stockings of those you love? Head the Berkshire Botanical Garden Holiday Marketplace! Not only will you find great gift ideas from local creators, but live music, a crafts corner, and s’mores around the fire are just a few of the fun things to do while perusing the spectacular assortment of handcrafted designer wreaths at the Gallery of Wreaths.

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Take the Fam to Joyful Holidays Family Day

Located at the ever-popular Norman Rockwell Museum (a worthy place to visit any time of year, of course!) the Joyful Holidays Family Day is a sweet small-town family event featuring festive children’s book readings, an interactive gallery drawing experience, and a Winter Wonderland scavenger hunt. For the kids… and the kids at heart!

Take a Holiday House Tour at the Mount

Close up of gold ornaments on real christmas tree

American author Edith Wharton’s home, The Mount, is a gorgeous place to see any time of year, but during the holidays, this National Historic Landmark becomes a turn-of-the-century Christmas wonderland! Holiday House Tours at the Mount are self-guided, so you can move through this beautiful estate at the perfect pace for you and yours.

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Book a Stay at Red Lion Inn

Photo of Red Lion with Christmas lights and snow Stockbridge MA Christmas

Editorial credit: James Kirkikis / Shutterstock.com

One of the most gorgeous places to stay in Stockbridge is the Red Lion Inn, a quintessentially New England inn that features fireplaces, lush and comfortable bedding, and fantastic dining options, including a Christmas Day feast and a New Years Day feast. Also, Red Lion Inn is a participant in Christmas events in Stockbridge such as Wednesday Night Holiday Jazz, Caroling in the Winter Themed Courtyard, Santa Brunches, and more, so be sure to check out their December calendar!

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Marvel at Naumkeag’s Winter Lights

The historic estate of Naumkeag is a historical Stockbridge gem, with ornate architecture and lovingly landscaped grounds to ooh and ahh over all year-round, but during the holiday season, Naumkeag Winter Lights is one of the most spectacular light shows in the region. To take a beautiful estate like Naumkeag and then string it up with thousands of lights? There’s no way for this to be anything less than pure magic!

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Sip a Maple Latte at Stockbridge Coffee & Tea

Close up of latte art

Stockbridge Coffee & Tea is a delightful coffee, tea, and pastry shop that doubles as a used bookstore, making it an absolutely ideal place to go hunker down a bit if the weather outside is getting frightful! Enjoy one of their hot drinks and a croissant as you pick out your new favorite book. What is a better Christmas in small-town Massachusetts activity than this?

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Cozy Up in a Berkshires Cabin

When you think comfy, cozy, Christmas vibes, you probably think of something like you might find in one of these Berkshires vacation rentals! There are so many fun things to do all around the Berkshires, choosing a vacation rental that situates you so you can easily see and do it all just makes sense, right?

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Shop Picturesque Downtown Stockbridge

The downtown that inspired Norman Rockwell’s “Home for Christmas (Stockbridge Main Street at Christmas)” is also a fantastic place to go get some Christmas shopping done! With unique boutiques and art galleries featuring local artists, you will most definitely find the best Christmas gifts for everyone left on your list! 

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Attend Stockbridge Main Street at Christmas

Horse and carriage and vintage car at Stockbridge Main Street Christmas

Editorial credit: James Kirkikis / Shutterstock.com

The Christmas spirit of this lovely little Christmas town is never more evident than during their annual Stockbridge Main Street at Christmas festivities! See this lovely downtown with vintage vehicles parked along the street, recreating Norman Rockwell’s famous Christmas image. There’s a historic holiday home tour, caroling, and of course, Santa in a sleigh! The very essence of a Stockbridge MA Christmas can be found in this annual event.

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There are so many fun and festive ways to spend Christmas in the Bay State, the hardest part is picking the perfect spot for your Christmas vacation in Massachusetts!

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