Stockbridge, MA: Wintertime in the Berkshires

Stockbridge, MA: Wintertime in the Berkshires

My family and I recently went to the Berkshires during record low temps – think negative 20 degrees – and many people were at a loss as to how to approach their long-awaited ski plans, including us. But with a little research, we came up with alternative plans that proved to be just as fun. We were headed to Jiminy Peak in Hancock, MA, but we opted to spend most of the weekend in Stockbridge, MA. And what a gem this little New England town is. In some ways I’m sort of glad it was too cold to ski!


To give some background, we had rented a house through Airbnb in Canaan, NY with two other families. We couldn’t stay at Jiminy Peak because we were arriving on a Saturday, and like most mountains, they required a Friday – Monday stay for the holiday weekend. So we found a spacious house in Canaan, close to the border of MA and about 20 minutes from Jiminy. We have been having luck with Airbnb ski rentals recently, as seen in another post on the Berkshires here.

Perched up on a hill overlooking the countryside and lake below, we had incredible views, especially at dawn and dusk. The house was equipped with a big wrap around bar and stools, kitchen with wood-burning stove, a “great” room with lodge-type feel, as well as a basement with large screen tv for the kids. It was perfect for our group. But with the biting cold and excruciating windshield, it took a long time for the house to fully warm up. It’s the type of house we could have lounged around in all day if it was just quite warm enough, but since it wasn’t, we decided to make Stockbridge, MA our destination for most of the weekend. And who are we kidding – with this crew, meaning my family, we weren’t going to hang out all day at the house anyways. If it wasn’t going to be skiing, it was time to go exploring!

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The Berkshires has many options as far as culture and quaint towns to check out – this western part of MA is filled with cute villages, museums and good food. We decided on Stockbridge because it was 15 minutes away from our house, set in a wonderfully scenic area of rolling hills and countryside, plus it’s home to the Norman Rockwell Museum, which I had long been wanting to visit. The town itself is as charming as they come, with cozy restaurants, country stores and artisan workshops. If you’re in the area during wintertime and are looking for some fun, or different, things to do other than skiing, see my list below:

Norman Rockwell Museum

Home to the works of iconic American artist Norman Rockwell. If you like his art, you will love this little museum. Norman Rockwell was born in New York, but moved to Stockbridge from VT in the 1950’s, having fallen in love with the area. It’s a good size to take the kids because it’s not too big – plus they have a kids’ Scavenger Hunt, which my girls loved. They went around searching for about 10 different paintings and answer questions particular to each painting; it was a great way to engage them with the art. Downstairs they have an arts and crafts section, and a video room where you can view the history of Norman Rockwell’s life. Hours: Weekdays, 10:00 a.m. – 4:00 p.m., Weekends and Holidays, 10:00 a.m. – 5:00 p.m. Admission: Adults, $18, Kids 6-18, $6, Kids 5 and under free. 9 Route 183, Stockbridge, MA, 01262, 413.298. 4100, etx. 221

You may also enjoy: Beautiful Berkshires: A Driving Tour



The Red Lion Inn

This historical inn dates back to the late 18th century, when it first opened as a tavern with guest rooms. Having undergone several expansions and different names over the years, it always featured a red lion in its sign. The inn is famous for its collection of antiques and decorative arts (one of the owners was an avid collector, continued years later by another owner), as well as its inviting long, outdoor front porch. In addition to guest rooms, it has a tavern, Main Dining Room, and the Lion’s Den bar and lounge. And then of course there is the Main Lobby and Side Parlor, where you can enjoy a roaring fire and live piano music.

Each of the rooms is a trip to walk through, as you go back in time to another era. I especially liked the old telephone booth rooms, which I believe are still in use with modern phones. While we waited for a table for lunch in the dining room, we drank Bloody Mary’s in the tavern, and I swear it might be the best bloody around. Our lunch was delicious, comfort food and hearty, great for a freezing cold day. Last but not least by the gift store they have a big chess table, where my older daughter and husband were able to warm up with a competitive game. We loved The Red Lion Inn and will definitely be returning. 30 Main Street, Stockbridge, MA, 01262. 413.298.5545



 Once Upon a Table

This sweet, tiny restaurant consistently gets voted as one of Stockbridge’s most popular eateries, and we can see why. The food is simple, but very good. We ate lunch here on a whim when we had just driven up from the NYC area in the bitter cold. A steamy carrot ginger soup was just what I needed, along with a mozzarella, pepper, tomato and pesto sandwich on the freshest of focaccias. Make sure to order their signature profiteroles for dessert – pure insanity. 36 Main Street, Stockbridge, MA, 01262. 413.298. 3970

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Williams & Sons Country Store

One can while away some time at this classic small town country store. Walk into a trip down memory lane as you sift through old school trinkets, gifts, home accessories, bath products, etc. And if you follow my blog you know that I love candy! Especially the nostalgic kind, which this store displays so well. 38 Main Street, Stockbridge, MA 01262. 413. 298.3016



 Other Winter Activities near Stockbridge:

 Cove Bowling and Entertainment 

There’s nothing special about this bowling alley, but when it’s negative 20 degrees, it’s great to know you have one near you. It was PACKED. There’s also a mini golf course and arcades inside. Go on the early side if bad weather. 109 Stockbridge Road, Great Barrington, MA, 01230. 413.528. 1220


Furnace Brook Winery at Hilltop Orchards

Located in nearby Richmond, the bucolic hilltop setting of this winery and orchards is a nice, easy time-filler for a non-skiing day (and I’m sure even moreso in the warmer months). Try 5 tastes for $5 and get a 6th one free. The server was so nice I think I got about 9 tastes when all was said and done. And the wine was not bad! Actually, the port was amazing. We purchased a bottle of that along with a couple others. How do you keep the kids occupied? With their delicious apple cider donuts and baked goods. Rt. 295/ 508 Canaan Road, Richmond, MA, 01254, 800.833. 6274.


We did finally make it to Jiminy Peak our final day, Presidents day, and loved it. See my guide to Jiminy Peak here.

This article is available as an app through GPSMyCity if you would like to read it offline whenever and wherever. Click here to download the city app, as well as for GPS coordinates of the locations listed.



  1. Jenny Jaffe
    February 19, 2016 / 1:27 am

    Great post!

  2. February 19, 2016 / 9:36 am

    The weather is so strange. Difficult for tourist industry though sometimes it makes you try something new.

  3. February 19, 2016 / 12:15 pm

    Sounds like a pretty perfect weekend to me – what a gorgeous place with so much to see and do, I love it!! Weird weather seems to be the norm here too though unfortunately….

    • February 19, 2016 / 2:16 pm

      Yeah I guess you should always have back-up no matter where you are. Lesson learned!

  4. February 22, 2016 / 8:56 am

    What a picturesque place! I also love candy, especially when the pieces are individually wrapped and displayed in big jars like back in the old days. It looks good as decoration too:)

    • February 23, 2016 / 3:32 pm

      Totally – it just makes a place look happy and inviting..

  5. February 24, 2016 / 10:49 pm

    Well, it does look a beautiful place to spend time but the absence of snow is always a bonus for me 🙂

    • February 25, 2016 / 5:41 am

      Ha – that’s right. I like snow in certain doses but too much of it can drive one mad..all the shoveling alone!

  6. February 25, 2016 / 1:14 pm

    Looks a lovely place and lots of great info for anyone planning a break here! The Red Lion Inn looks delightful 🙂 Can’t get my head around how cold it must have felt! We are just starting to get an autumnal feel here at night – it has been dropping down to around 11 or 12 degrees and we think that is it on the cool side!!

    • February 25, 2016 / 4:10 pm

      I’m so over winter and yet I have nothing to complain about – with the exception of that terrible cold weekend – because it’s been unseasonably warm here. I guess i’m just over the gray skies and jacket weather – want to feel light again!

  7. February 28, 2016 / 1:26 pm

    I like that you got 9 tastes! I’m sure that it warmed you up in those freezing temps. Can’t even image -20, and I thought Iceland was bad! That’s the beauty of travel though isn’t it – when one plan doesn’t work out you think of another and it often ends up being great too – Berkshire looks so pretty.

    • February 29, 2016 / 3:08 am

      It’s so doesn’t always go as planned as well all know – open mind necessary;).

  8. March 1, 2016 / 8:14 am

    The town looks quaint and picturesque, and the AirBnB accommodation looks very inviting and comfortable. If the house warms up easily, I wouldn’t mind holing myself up in the house throughout the weekend 🙂

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