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Cabin Fever? Try a Berkshires Winter Getaway!

Berkshires Winter Getaway - Winter Landscape
Matt Claiborne
Matt Claiborne
January 28, 2022

If the winter blues are getting you down, one of the best pick-me-ups is to head outside and embrace the winter wonderland. Pittsfield offers a variety of winter sports across hundreds of venues.


Whether you like to sit by the fire, get out and ski, or enjoy a mixture of both, the Berkshires offer endless winter fun. Get a lift to the top of the mountain and enjoy downhill skiing. Or, choose from dozens of state parks and state forests and go cross-country skiing or snowshoeing.

The Pittsfield area offers a variety of trails and open spaces for snowmobiling. Enjoy views from the highest mountains while you explore adventurous trails.

In addition to outdoor fun, visitors can enjoy the local orchard, taste apple cider, and warm up by the log fire.


Bousquet Mountain

Bousquet Mountain is the ideal place to head for winter sports. Bousquet Mountain offers downhill skiing, snowboarding, and snow tubing. Bousquet Mountain has three lifts and two carpets.

In addition, the ski area offers night skiing. Visitors can buy day passes or season passes.

If you are a first-time skier or looking to improve your skills, Bousquet Mountain offers a variety of lessons and packages.

Guests can rent wooden cabana huts as a relaxing day base lodge. The cabanas have cloth curtains, seating for a family of four, a propane heater, and chocolate fondue.



Snowmobiling is a fun way to get outdoors and try something new. The Berkshires offer a wide variety of areas to check out. The site features dozens of state forests with stunning landscapes. Snowmobilers can enjoy forests, gorges, mountain views, and snow.

Pittsfield State Forest offers a beautiful landscape to snowmobile through. Pittsfield State Forest has 30 miles of trails, and many are perfect for winter sports. Snowmobiling in Pittsfield State Forest offers a rustic experience focusing on stunning scenery and rural trails.

October Mountain State Park features the beautiful Schermerhorn Gorge. Check out the different parks, ski fields, and resorts and be amazed at the variety of experiences the Berkshires offers.

Mount Greylock has a 3,491-ft peak and is the highest in the area. Mount Greylock offers miles of trails and views of five states.


For a non-snow sports experience, check out the family-run Hilltop Orchards. No trip is complete without this winter getaway highlight. The orchard features breathtaking views, and on a clear day, visitors can see three states.

Warm up with a wine tasting, apple cider treat and try a cider donut. Then, relax by the wood-burning fireplace or take a cidery tour. In the cidery, fresh apples are turned into cider. Hilltop Orchard performs every step on-site.

Hilltop Orchards is also a great place for snowshoeing. They have miles of groomed terrain and offer moderate and challenging trails. In addition, the Snowshoe Trek & Bonfire is a popular winter event.



Kennedy Park is a fabulous park with almost 15 miles of groomed trails. Visitors can enjoy cross country skiing or snowshoeing on old carriage roads in this hardwood forest.

Most of the park's trails are smooth and flat and make great snowshoeing and cross country skiing treks. However, visitors should be aware that the trails aren't groomed.

The Arcadian Shop has rentals available.


Winter in the Berkshires offers snow sports and outdoor fun. Stay warm in one of our cozy Hotel on North rooms and enjoy your winter escape.