Getaways

Getaways: The Berkshires

The Berkshires in western Massachusetts has a lot to offer skiers and foodies alike.


When you live in NYC and you want to getaway, there are a few areas locals tend to go in the summer and winter: The Hamptons, the Catskills and the Berkshires. In the winter, the Berkshires make sense as it’s also an easy driving distance for skiing.

Scott and I both ski well. We skied a lot as teens and in college locally and then out west in Colorado, California, Utah, Wyoming, Idaho and New Mexico. Scott’s girls however have not gone as frequently as we did. Given a choice of skiing or beach, they easily would pick beach for a vacation.

The past weekend was Martin Luther King Weekend. Traditionally this weekend is peak for weekend skiing here in the Northeast, snow and weather permitting. Given we are still in the middle of a pandemic and we are all due for some fresh air and scenery we decided we would take the girls skiing in the Berkshires and stay at an AirBnB.

Our AirnBnB

I grew up skiing at Butternut Mountain. When I was a teen, my mother would drop my younger brother, Daniel, and I off at the base of the mountain at 8:30am on a Saturday and we would be done around 3pm. Occasionally, my parents would let me go with my friend Jessica and stay at the cabin in South Egremont by ourselves. For this trip, I selected Butternut Mountain so Emma and Davin could ski with their cousins who have season passes (socially distanced of course). The mountain was quieter on Saturday due to a wintry mix but Sunday was a typical holiday weekend – very busy.

Mountains/Ski Resorts: Butternut Mountain is our family favorite. However, Catmount and Jiminy Peak are all close by. If you want a week-long ski adventure you likely will head to Vermont but if it’s just for the day these 3 are perfect. During the pandemic you need to book everything online due to capacity limits. However, during more normal periods it’s so much faster to book/pre-pay online.

Dining In/Out: Right now there are not too many options for dining in. But below are my favorite restaurants in the area.

  • The Old Mill: I have eaten here more times than I can remember. I think we went every weekend as a family for a while and certainly on Christmas Eve and New Year’s Eve as well. Solid food in a wonderful restored grain mill. Go for dinner indoors when the pandemic is over and for now order ahead and pick-up.
  • Six Depot: Located in West Stockbridge, MA they have amazing organic breakfast menu. Weather permitting you can sit outside with heaters or otherwise order ahead and eat at home.
  • The Lost Lamb: Is a wonderful new addition to Stockbridge. With breakfast pastries, baguette sandwiches and delicious looking cakes made with love by Le Cordon Bleu trained Pastry Chef.
  • Starving Artist Cafe: Suggested by my sister in law had delicious soups and crepes. Scott and I felt they had generous portions and it was just what we were looking for.
  • Betty’s Pizza Shack: In Lenox, this chef opened this fabulous pizza and burrito shack after visiting Costa Rica. We ate pizza by fire pit on my in-law’s property in the snow.
  • Cafe Adam, Bar and Restaurant: Located in Great Barrington, MA. The restaurant serves a seasonal menu peppered with local ingredients. They have pre-pay and pick-up on Resy and take limited reservations for outdoor dining.
  • Barrington Brewery: Great Barrington, MA. Stand-out BBQ with a wide selection of beers and a terrific Chocolate Stout Cake.
  • The Red Lion Inn: Located right on the main street in Stockbridge, MA. This is the grand dame hotel/Inn of the region. With its big white columns, porch and afternoon tea. It’s old school and symbolic go here for dinner but it’s not my favorite.
Crepes for Lunch

Foodie Finds: The area is known for its amazing local purveyors from bread to cheese to ice cream and coffee.

  • Berkshire Mountain Bakery: The Bakery/Shop is located in Housatonic, MA. They have amazing breads like chocolate, cherry pecan and their fresh sourdough was featured on the Netflix show Cooked. They also have a pizza shop in Pittsfield.
  • Six Depot: Stock up on provisions now and have extra items to bring home. Their roasted coffee is excellent you can also grab a cup to go.
  • Patisserie Lenox: Beautiful baked items from croissants to cakes located in Lenox and Great Barrington, MA.
  • SoCo Creamery: Are you dreaming of ice cream? Then this is your oasis. Even in winter it always packed. Visit the store in Great Barrington, MA.
  • Nejimes Wine Cellar: He opened his first store in Great Barrington, MA in the 80’s and has been serving visitors and locals goodies for Tangelwood and country homes ever since. Good solid wine selection. There is also a cheese shop is next door.
  • High Lawn Farm Creamery: We received a cheese box from them this past Christmas (2020). What an incredible gift. Their cheese is mostly butterfat and so rich and decadent. Visit the creamery for cheese, jams, pate, crackers, blended honey, maple syrup, fresh milk and eggs and ice cream. Pairs well with the Berkshire Mtn. breads.

Other Shopping: There are many cute towns to visit and shop: Great Barrington, Lenox, Lee, Stockbridge, and West Stockbridge all have local shopping at various price points. For Ski Gear: My family and Scott’s brother who lives in area have been going to Kenver in South Egremont for years. It’s not the cheapest but the family owned business is the best in the area.

While this post is mainly about winter activities, the area is also wonderful in the summer. From hiking the local trails at Monument Mountain and Bish Bash Falls, to outdoor concerts at Tangelwood and seeing a play at the Berkshire Theater Group. I promise to update the post come summer!

Love outdoor activities try an outdoor hike anytime of the year.

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