Dylan in the Details is a travel interested in culture, history, and giving you the best recommendations for your next trip!

Small Town Spotlight: Christmas in Stockbridge, MA

Small Town Spotlight: Christmas in Stockbridge, MA

While I love trips to huge cities or faraway lands, I also find myself constantly falling in love with small towns. Whether you’re looking for a weekend trip or a stop on a road trip, Small Town Spotlights is a collection of my favorite hamlets across the country.

While you could probably make a decent argument for spending Christmas in any city in the world, I personally don’t think there’s a better place to spend the holidays than in a small town in New England. Yes, it will be cold. If you’re lucky, it may even snow. Even without a darling dusting of snow, there is something about colonial houses illuminated by Christmas lights and the mountains rising of the grey horizon that makes it truly feel like Christmas. (Or maybe it has less to do with the lights and mountains, and more to do with the fact that I was raised there? Either way, I’m still right.)

There are plenty of charming small towns scattered throughout the Northeast, but Stockbridge, MA has a special Christmas connection that puts it in its own category of Christmas magic. Not only does the town get dressed up every year, but it was immortalized in all its glory by famous painter Norman Rockwell in 1967. (You can see the painting here at the bottom of Stockbridge’s 2018 Christmas schedule.) Stockbridge is the only place where you can a Rockwell Christmas along with the rest of your holiday cheer.


Norman Rockwell Museum

Before heading to downtown Stockbridge, you first have to check out the museum dedicated to the man himself. Famous for painting scenes depicting American life from the 1930s-1970s, you have probably seen his work on old magazine covers, plates, and other such things. There’s a pretty good chance, upon seeing his work, you’ll recognize the style nod knowingly. He’s the guy you didn’t know you would know. Also be sure to visit his studio (pictured below), that has been moved and preserved behind the museum


Norman Rockwell Grave

If you leave the museum and are feeling inspired, you can go pay your respects at the Rockwell grave in Stockbridge Cemetery. He’s in the back, partially hidden by large rectangular hedges right in front of a huge row of trees

normal rockwell grave

 Downtown Stockbridge

After an afternoon at the museum you’ve learned about Rockwell and experience his works. (Let’s be real, unless you’re really  into art, you probably saw more of his works than you ever wanted to.) Now its time to see the real thing. Here’s the tricky thing about Stockbridge, some of the businesses tend to close fairly early. Even though the Christmas decorations look best at night, I would head down while it is still light and you can wander throughout the stores. Once you’re done with that you can have dinner (see recommendation below) and then walk the street again after dinner. (If you’re not interested in shopping, then I’d be less worried about what time you arrive.)

Downtown Stockbridge

 The Red Lion Inn

In the spirit of having a Stockbridge Christmas, I can’t send you anywhere else for dinner other than the Red Lion Inn. Located on the corner (and the far right of Rockwell’s painting), the Red Lion Inn has been around since the late 1700s and is a landmark in its own right. With three types of dining options, The Main Dining Room, The Tavern or the Lion’s Den, check their website for a menu (and  price range) that you’re comfortable with.

the red lion inn


Barrington Brewing Company

Just in case the Red Lion Inn isn’t quite your style, my bonus recommendation is to drive ten or so minutes South of Stockbridge to Great Barrington and check out the Barrington Brewing Company. Serving homemade beer, this place takes sustainability as seriously as they take their local roots. With solar panels and other systems generating most of their energy, and aging coasters and snarky posters tacked up on the wall, you’ll feel like you’ve walked into the combination of hippie and asshole that makes Massachusetts famous.


Have you been to Stockbridge? Do you have a favorite place to spend the holidays? Let me know in the comments!


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