A Winter Weekend In Great Barrington, MA!


I feel like summer weekends get all the hype…but there’s definitely something to be said about winter weekends, too–even if snow sports aren’t exactly your jam (they’re definitely not mine;-)  We took advantage of the long MLK weekend and headed north about 3 hours to Great Barrington, MA–otherwise known as The Berkshires.  Now, if you’re a longtime reader you’ll probably recall we’ve written about a weekend getaway to The Berkshires before, but that was during the high season (i.e. summer.)  I wanted to share our little itinerary here in case any of you are looking for a quick getaway during these next few chilly months!

Where To Stay

We opted to stay at The Briarcliff Motel, and couldn’t have been happier.  It’s exactly what you think of when you hear the word “motel” (yes, outdoor corridors and all), but thanks to the new(ish) European owners, it has a super cool hipster vibe to it.  So you kind of feel like your visiting your friends in Williamsburg, Brooklyn!  The rates are great (we paid $150 a night for the weekend), a homemade breakfast is included (definitely try the scones), and a really cool touch is they have a barrel of DVD’s you can choose from to have a movie night in your room!  The common area is also a nice touch if you’re traveling with a group like we were.

We also loved gathering around the bonfire in the evening with our plastic cups of wine.

Where To Eat

Here’s a list of places we enjoyed!

Brickhouse: This came recommended from both another blog and the owner’s of the motel.  I’ll start with the positive first: it had a local Berkshires vibe, amazing pizza with crust made by the Berkshire Mountain Bakery, live music on Saturday nights, and is casual enough to bring kids.  However, it was probably the slowest service I’ve ever had in my life.  No lie, we waited two hours for our food to come out, which was basic pub fare.  Maybe they were just having an off night, so I don’t want to totally discredit them, but if you’re in a hurry, consider going elsewhere.

Stockbridge Coffee + Tea (and book store!): Lavender hot chocolate or maple latte, anyone? Plus a connected gently used bookstore, always a plus in my book!

Rubi’s Cafe: This spot was a favorite of mine, because they have a variety of grilled cheese sammies, make a fantastic hot cocoa, and had a real live crackling fire in the fireplace.  It’s super casual, and perfect for lunch!

Lion’s Den: We went here on our last trip to The Berkshires and loved it so much we returned.  They have a great lineup of live music 7 nights a week, so you’re always in for a treat, and yummy pub fare.  The lemon hummus and hot apple cider with bourbon were table favorites!

Domaney’s: This is a wine store, but the best one in town, we were told!  So if you need to stock up on some vino for evening fireside fun, head here!

To Do

If you enjoy skiing, snowboarding, or tubing, you definitely should head over to Butternut, which has it all and is about a 15 minute drive from the motel/town.

They also had a local Farmer’s Market while we were there (don’t worry, the market is inside during the winter months!)  You can stock up on locally made soaps, honey, chocolates, and listen to jazz music.  The schedule seems to vary, but you can check ahead of time here.

One of my personal favorite things to do was check out the incredible vintage stores in the area–they have it all, high end to fabulously cheap finds, and SO MANY OF THEM.  Really, all you have to do is take a drive into town and you’ll see them on both sides of the road.  Two I particularly loved were the Yellow House Books, selling used and rare books, and Chelsea & Co., where I found an original vintage Irish fisherman’s sweater–something that has been on my list for the longest!

And of course, you can’t beat a museum on a cold day!  The Norman Rockwell Museum is a local favorite and has something for all age groups.

That about wraps up our trip to Great Barrington!  Oh!  And while you can technically take a bus up here, cab service isn’t something widely used, so I would suggest renting a car for the weekend–it will make your trip much more enjoyable.

I’d love to know–do you have any favorite winter weekend getaways?  Share below!


  • Joanne says:

    Glad you stayed at the Briarcliff – great locale, good people – from the Lake District of England, I recall?
    The Berkshires is tops on my list of favorite getaways. Such a gentle, genteel world up there, so much to do and see, but tricky in the off peak months as some sites (for instance, Melville’s home “Arrowwood” ) close for the season, so always check.
    Agree, a car is a MUST.

  • Tracy Kaler says:

    Love love love Great Barrington. Been there a few times but have not stayed in the town itself. Need to do a weekend and stay there. It’s got a great vibe, and is in a beautiful part of the state. This post makes me want to pack right now and head for the Berkshires!

  • Tamara says:

    You know, despite only living about 45 minutes from Great Barrington, I’ve only been there once! It was a very hot day, unlike you experienced, but we totally loved it. We did get coffee at Rubi’s! Then we explored some toy and bookstores, and had lunch at a place with an arcade! I think it was called Gypsy Joynt or something like that?
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  • Adna says:

    Love this!! The perfect weekend getaway! 🙌🏼🤗

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