Five Fun Off-Season Things to Do in the Berkshires

Cozy seating area with a white couch and pink chair in front of a fireplace. Summer may be over and fall winding down, but the Berkshires still offer plenty of fun things to do in the off-season. Whether you’re angsting about the upcoming holiday season or just looking to get out of town for a change of scenery, the Berkshires is the perfect destination for a respite. In under three hours you can shed the hubbub of Boston or New York and land in the lap of comfort and serenity at the Staveleigh House Bed and Breakfast in Sheffield, MA. Beyond the cozy environs of the Inn itself lies a world of natural beauty, history, arts, culture, music, and more. Amp up your playlist and head to the hills for an off-season adventure indoors or out.

Art and Culture
When the weather says “Baby, it’s cold outside” opt for indoor entertainment to inspire the senses. Whether it’s dance, art, music or theater that sets your soul on fire, you’ll find it all year round in the Berkshires. Jacob’s Pillow, Shakespeare and Company, and the Mahawie Theater are but a few of the venues offering performances and/or tours throughout the year. Several significant museums dot the countryside as well, so no matter if you’re a fan of contemporary art or prefer the Old Master’s, you’ll find something to suit your taste here.

Food and Drink
Not much can compete with an extraordinary meal or an exquisite cocktail in a new found restaurant or bar while on an off-season getaway. When there’s a chill in the air, hearty soups and stews can instantly warm, especially when chased down with a mellow glass of wine. The many towns and villages of the Berkshires don’t disappoint in this regard. Check out our list of favorite haunts in our blog post “The Best Restaurants in the Sheffield, MA area”.

Get Outside
Snow on the ground or leaves underfoot, hiking or snowshoeing is an excellent way to enjoy the outdoors. Skiers will want to test their skills at Butternut, Catamount, Bousquet, Berkshire East, or Jiminy Peak. Downhill not your thing? Try Canterbury Farm for cross country skiing or snowshoeing. And for ideas on where to hike, check out our commentary on Hiking Race Brook Falls Trail or Hiking the the Berkshire’s Campbell Falls State Park.

Learn Something New
Rev up the brain cells by becoming a Reiki master, embracing the mindfulness movement, or connecting with nature through forest bathing. These are among the offerings at the Kripalu Institute in Stockbridge, MA when you purchase a day pass. The Berkshire Botanical Garden offers tons of workshops, lectures, and educational classes to feed the heart and soul all year long. And at the Norman Rockwell Museum you can hone your artistic ability with a hands-on one day art class.

Up the Romance
Nothing can flame the fires of romance like an intimate retreat to the mountains for a soothing bed and breakfast getaway. Quiet and cozy, comfortable and relaxing, let the innkeepers at the Staveleigh House Bed and Breakfast spoil you with gourmet breakfasts and a perfect cup of coffee to start your day.

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