Like many people, I was first drawn to the Berkshires by a summer concert at Tanglewood. An outdoor performance of “Star Wars” music, with John Williams conducting the Boston Pops and a picnic basket full of treats, was an easy sell for my young children.
Since then, I’ve been coming back to the Berkshires for almost a decade and even lived there for a few years. What keeps me returning to this westernmost area of Massachusetts is its unique blend of outdoor activities, culture, literary heritage and farm-to-table food, all with an unfussy vibe. Here’s how I’d spend a weekend in the Berkshires beyond hiking and camping.
Outdoor activities
The Berkshires offer year-round activities. In winter, there’s skiing at Bousquet Mountain, Jiminy Peak and Butternut. For cross-country skiing, Notchview offers 25 miles of trails, including groomed routes, and a cozy lodge with a fireplace. In fall, head to Hilltop Orchards for apple picking and cider tasting. Its 200-acre property also has woodland trails to explore on foot or snowshoes, depending on the season and conditions.
For a high-octane thrill, Catamount, which straddles the New York-Massachusetts border, offers an aerial adventure park in the woods and the CataMonster zip line, billed by the resort as the longest dual zip line in the United States. These attractions operate seasonally, so check the schedule before planning your trip.
The Ashuwillticook Rail Trail offers a family-friendly bike ride along about 15 miles of paved path between Pittsfield and Adams. Choose a shorter out-and-back if you don’t want to ride the full distance.
When you need to cool off in warmer weather, rent a paddleboard or kayak from the Arcadian Shop and arrange delivery to the public boat ramp at Stockbridge Bowl, also known as Lake Mahkeenac.
Where to shop
One of the newer places to shop is Walker Street Market in Lenox, a design gallery showcasing works from about 70 artists and makers, including paintings and ceramics.
Stop by the Arcadian Shop next to Kennedy Park in Lenox for outdoor clothing and gear. Main Street in Great Barrington is packed with boutiques, including Fluff Alpaca for cozy sweaters and Westerlind for gear that is as technical as it is stylish.
Culture
The Clark Art Institute in Williamstown is a classic Berkshires experience combining art and the outdoors. Explore the Impressionist paintings in the main building, then head outside to enjoy the meadows and walking trails on its 140-acre campus. Carve out at least half a day to explore the Massachusetts Museum of Contemporary Art in North Adams, one of the largest contemporary art museums in the country. Its campus occupies a 26-building former factory complex.
Book lovers can indulge at The Mount, the former home of Edith Wharton. She worked with architects on the grand mansion and designed its elegant gardens, drawing on English, French and Italian influences. Herman Melville fans should sign up for a guided tour of Arrowhead, where he wrote “Moby-Dick.” Check tour schedules at both houses before visiting, as availability changes with the season.
Where to stay
Accommodations range from ultraluxurious spa resorts such as Canyon Ranch and Miraval Berkshires to design-forward stays at The Porches Inn at MASS MoCA and Prospect Berkshires.
An elegant option is Garden Gables in Lenox, a 16-room boutique hotel in a historic house within walking distance of the town’s shops and restaurants.