A Perfect Winter Weekend In The Berkshires: What To Do This Winter In The Berkshires

Welcome To Winter In The Berkshires

Summer may have hydrangeas everywhere and a top-notch farmer’s market but there’s something exceptionally charming about the winter months in the Berkshires - and there’s still plenty to do.

Pop Into A Dare Bottleshop and Provisions in Lenox

There’s a new wine and provisions shop in Lenox called Dare Bottleshop and Provisions. Be on the lookout for free wine tastings.

Make A Reservation At Old Inn On The Green

This candlelit restaurant is all the more special in the winter months. The fireplaces are lit, the pre-fixe menu (three courses, $65) features heartier options and a bottle of sommelier recommended red wine is even better when it’s freezing outside.

The Perfect Breakfast At Home

The Warm Welcome kitchen is totally stocked, so all you need to do is pick up the fresh ingredients from our local stores. We recommend a visit to Guido’s for local eggs and Berkshire Mountain Bakery for fresh bread and pastries.

Farm Fresh Meats

Add some fresh bacon of breakfast sausage to our spread with a visit to North Plain Farm. This farmstand is open every day and works on an honor system - you can always bet they’ll have an amazing selection of frozen meats and more ready for you to bring home.

More Than Wine

A visit to Départ on Railroad Street in Great Barrington is a must - even if you don’t drink. They have a great selection of wine and local goodies like this adorable Pioneer Valley Popcorn.

Ski (or Snowboard) Butternut

Just two minutes away from Warm Welcome Great Barrington is Butternut, the Berkshires’ affordable family mountain. If you visit during the week, you can get even better rates on your lift ticket.