Things to Do in the Berkshires (Offseason)

As the leaves fall and the snow begins to blanket the hills, the Berkshires transform into a winter wonderland filled with cozy charm, outdoor adventure, and small-town magic. Whether you’re planning a long weekend escape or an extended stay, there’s no shortage of things to do in the Berkshires from November through March.

From festive holiday events to world-class skiing and intimate fireside dinners, here’s your guide to making the most of the Berkshires’ quiet season.

Hit the Slopes

Winter sports lovers flock to the Berkshires for some of the best skiing and snowboarding in New England.

• Jiminy Peak (Hancock): The largest ski resort in the region, offering 45 trails, night skiing, and an alpine coaster.

• Bousquet Mountain (Pittsfield): A family-friendly mountain that’s perfect for skiers and riders of all levels.

• Catamount Mountain (Egremont): Straddling the MA/NY border, Catamount offers great trails and a cozy base lodge.

• Otis Ridge: A smaller, old-school ski area with local charm and affordable lift tickets.

If you prefer a slower pace, explore cross-country skiing or snowshoeing at places like Canterbury Farm, Notchview, or Hilltop Orchards.

Explore Winter Hikes and Scenic Drives

When the snow glistens across the hills, the Berkshires’ trails take on a new kind of beauty.Bundle up and take a winter hike at:

• Monument Mountain (Great Barrington) – A moderately challenging hike with breathtaking views.

• The Ashuwillticook Rail Trail (Lanesborough to Adams) – A flat, paved trail perfect for winter walks.

• Greylock Glen (Adams) – Offers stunning views of Mount Greylock, the highest peak in Massachusetts.

Prefer to stay warm? Take a scenic drive through Stockbridge, Lenox, and Williamstown, where twinkling lights and snow-covered streets create postcard-perfect moments.

Cozy Up Indoors

Cold weather calls for cozy vibes — and the Berkshires deliver.Spend an afternoon exploring local favorites like:

• The Clark Art Institute (Williamstown) and Mass MoCA (North Adams): Two of the best art museums in the country.

• The Mount (Lenox): Edith Wharton’s home, beautifully decorated for the holidays.

• Norman Rockwell Museum (Stockbridge): A must-visit to experience the charm of small-town Americana.

Then, unwind with a fireside dinner at local gems such as Mezze Bistro + Bar, Old Inn on the Green, or Alta Restaurant & Wine Bar in Lenox.

Holiday Magic in the Berkshires

From late November through December, the Berkshires shine with festive cheer.

• Stockbridge Main Street at Christmas: Step into a Norman Rockwell painting with carolers, horse-drawn rides, and twinkling lights.

• Berkshire Botanical Garden’s Holiday Marketplace and Naumkeag’s Winterlights offer magical family experiences.

• Downtown Great Barrington and Lenox also come alive with local shopping events, artisan markets, and hot cocoa stops.

Sip, Taste, and Relax

Winter is the perfect time to slow down and savor local flavors.Visit a craft brewery like Big Elm or Shire Breu-Haus, or sip a glass of wine at Hilltop Orchards in Richmond. Many spots offer cozy tasting rooms and seasonal treats.

And don’t miss the Berkshire Food & Wine Festival events or farm-to-table dinners that pop up throughout the season.

Stay Warm with Berkshire Hosts

Whether you’re looking for a romantic getaway, a family ski weekend, or a peaceful escape from city life, Berkshire Hosts offers handpicked vacation rentals across the region — from mountain-view cabins to modern downtown stays.

Each property is locally managed for comfort, cleanliness, and that touch of Berkshire charm.

Plan Your Winter Escape Today

The Berkshires in winter offer something truly special — a blend of nature, culture, and coziness you won’t find anywhere else.From November through March, come see why travelers keep returning season after season.

Explore stays at BerkshireHosts.com and plan your perfect winter getaway.