Winter in the Berkshires

Thinking about a weekend trip to the Berkshires? We’ve put together a sample itinerary featuring Massachusetts history, scenic vistas, and a cozy inn.

Field Farm

Day One

Book your stay and snuggle up at Field Farm Guest House in Williamstown MA, offering an authentic mid-century-modern Bed & Breakfast. Now through December 29, stay two nights at the Guest House at Field Farm and get one night 50% off. Stay for three nights for the price of two. Details and more here.

Check in and enjoy a snowy walk around the property or trek over to Counterculture by Rose B. Simpson  before heading out to dinner in downtown Williamstown. Some favorites include Mezze and Coyote Flaco.

After dinner, enjoy time in front of the cozy fireplace in the living room or head to your room for a glass of wine and a view of Mount Greylock.

Sandy Seated in A Square

Field Farm Living Room

Day Two

Wake up at the stunning Field Farm and plan for your day at Notchview.

Right now Ski Notchview is offering an Early Bird Season Pass for only $49 per adult (early bird pricing until December 6, 2022) and $30 per youth! You must be a Trustees Member to purchase a season’s pass. Not yet a Member?  Join and purchase your pass at the same time!

With more than 3,000 acres of rolling terrain and miles of groomed ski trails, Notchview, a part of the Hoosac Range in the Berkshire Hills, offers an idyllic escape all year round—but especially in winter. Much of Notchview sits above 2,000 feet; Judge’s Hill, the highest point, is 2,297 feet. Most of the reservation is covered with a red spruce and northern hardwood forest. You can also snowshoe alongside the ski trails or go off track and explore the backcountry.



Day Three

After another delicious breakfast at the Guest House, plan to head into Williamstown or nearby North Adams for some world class art, including the Clark Museum and Mass MoCA.

If you are ready to venture further south, don’t miss Winterlights at Naumkeag, a dazzling display of holiday lights and experiences.

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