The Berkshires
Some of the activities you can do.
Tanglewood
Tanglewood is a music venue and festival in the towns of Lenox and Stockbridge in the Berkshire Hills of western Massachusetts. It has been the summer home of the Boston Symphony Orchestra since 1937. Tanglewood is also home to three music schools: the Tanglewood Music Center, Tanglewood Learning Center, and the Boston University Tanglewood Institute. Besides classical music, Tanglewood hosts the Festival of Contemporary Music, jazz and popular artists, concerts, and frequent appearances by James Taylor, John Williams, and the Boston Pops Orchestra.
Jacob’s Pillow
Jacob's Pillow is a dance center, school and performance space located in Becket, Massachusetts, in the Berkshires. The organization is known for a Summer dance festival. The facility also includes a professional school and extensive archives as well as year-round community programs.
Berkshire Botanical Garden
The Berkshire Botanical Garden, is a 15-acre botanical garden in Stockbridge, Massachusetts, United States. Its collections contain over 3,000 species and varieties, with an emphasis on plants that thrive in the Berkshires. Also hosts workshops not only for those who enjoy coaxing new life out of the soil but also for artists, cooks, and kids.
Museums
When you’re lost in the meticulous detail of an original painting or Saturday Evening Post cover at the Norman Rockwell Museum in Stockbridge or in the evocative boldness of a contemporary installation at MASS MoCA in North Adams, you won’t care if the landscape outside looks black and white. Art repositories aren’t the only Berkshires museums that stay open all winter. The Berkshire Museum in Pittsfield, with its array of galleries devoted to art, nature, and innovation, is undergoing dynamic transformation. Interactive experiences, such as those featured within the high-tech Curiosity Incubator, hint at what’s to come.
In Williamstown you have the Clark and now’s the perfect time for quietly exploring our permanent collection galleries or wandering the walking trails across our 140-acre campus.
The Mount
The Mount — the Berkshires’ preeminent historic house museum, where Edith Wharton wrote her most beloved novels — is also open for tours on winter weekends through February. Set as it is in a glorious landscape, the estate is an inspiring place for a winter’s walk or snowshoe trek, as well.
The Mount is a historic house museum and vibrant cultural center with a variety of tours, programs, and events for you to enjoy.
The Main House is open for the season daily from 10 am to 5 pm. Please note that special events may affect our hours.
The gardens and grounds are free and open daily from dawn to dusk.
Experience Night Wood at the Mount (wintertime)
November 17, 2023 - January 6, 2024
NightWood is an innovative and immersive sound and light experience set against the backdrop of Edith Wharton’s historic home. Wander the illuminated 3/4-mile route through the woods and gardens for an otherworldly experience that evokes wonder and awakens the imagination. Don’t miss the new elements this year!
On Stage
Performing arts and entertainment in the Berkshires is first class. See new plays, favorite musicals, dance from around the world, and concerts in historic halls and on grassy lawns. If you love the arts, the Berkshires is for you!
Mahaiwe Performing Arts Center, Shakespeare & Company, Berkshire Opera Festival, Williamstown Theatre Festival
Live Music
A singer or band plays the Lion’s Den at the Red Lion Inn in Stockbridge 365 days a year. Order a drink and some comfort food, and enjoy this underground pub’s cozy vibe. Thursday nights are reliably lively at the Guthrie Center in Great Barrington, where there’s warm camaraderie among musicians at weekly Hootenannys. Close Encounters with Music brings mesmerizing chamber music performances to Great Barrington stages on select winter nights, too. When Tanglewood is closed for the winter, the Berkshire Bach Society ensures rousing classical music performances are part of the region’s winter scene.
*Don’t forget to check out the WHERE TO EAT section for restaurants with live music :)
Wine Tasting and Ciders
Balderdash Cellars The wine, music, views, and atmosphere are wonderful.
Hilltop Orchards in Richmond you can rent cross-country skis or snowshoes and explore the property before heading inside for a tasting of Furnace Brook wines. Apple ice wine, made with fruit grown on-site, wouldn’t taste this smooth and sweet without winter’s deep freeze.
Sip Local Spirits and Beers
On winter Fridays and Saturdays, Berkshire Mountain Distillers in Sheffield offers tours of the first distillery opened in the Berkshires since Prohibition’s repeal. Its tasting room’s temptations include locally inspired, small-batch spirits such as Berkshire Bourbon Whiskey, made from corn grown two miles away. Big Elm Brewing is the Berkshire made craft beer that is distributed in Massachusetts, New York, Rhode Island and Connecticut. The Brewery Taproom in Sheffield, MA has various styles rotating on the 14+ taps, beer in cans to go and often has events from yoga and trivia to beer releases with food and music.
The Farmstead Creamery
Ice cream lovers should save time for a trip to The Farmstead Creamery at High Lawn Farm. Relax at their picnic tables with a scoop of coffee oreo or pineapple inside-out cake, or, if you’re in the mood for something savory, a cheese and charcuterie board.
Skiing, Snowboarding & Snowshoeing
The Berkshires are Massachusetts’s winter sports capital, where you’ll find beginner slopes and black-diamond trails at popular ski areas such as Ski Butternut, Catamount and Jiminy Peak. There are plenty of invigorating alternatives, though, for visitors who want rosy cheeks without snapping on skis. Easiest of all: Sit back and let gravity thrill you at one of the region’s snow tubing parks. Snowmaking keeps Ski Butternut’s eight-lane tubing hill primed for fun every winter weekend.
Rent snowshoes at Arcadian Shop or Berkshire Bike and Board, then crunch around Lenox’s Kennedy Park or choose your trail — from easy to challenging — at the Laurel Hill Association’s Stockbridge property. Cross-country ski through fields and forests at rural Canterbury Farm in Becket.
Hiking & Waterfalls
Berkshire County is a hikers’ paradise with trails that lead to scenic overlooks, peaceful meadows, and sparkling waterfalls.
Bash Bish Falls is the highest waterfall in Massachusetts and a popular scenic destination. The dramatic final pitch of Bash Bish Brook drops about 80 feet into an emerald plunge pool. Enjoy a hike to experience the wonder and beauty of this deep, verdant gorge. Nearby, Taconic State Park in New York state offers more visitor amenities, picnicking, and camping.
Umpachene Falls provides a serene haven for that well-needed break from the hustle and bustle. The lazy Konkapot river is safer for the children whilst adults can smoothly wade in the pools of Umpachene Falls. There are chairs and tables in the park for a pre-planned picnic at lunchtime. You will only be able to clearly spot the falls once you are about 300 feet from your vehicle, towards the rear end of the park. Don’t forget to pack a picnic, bring slip-resistant shoes for the slippery rocks and a portable hammock with tree straps for the ultimate chill out day!
If you’re planning a day in Lenox a walk at Mass Audubon’s Pleasant Valley Wildlife Sanctuary is lovely. Trails wind through over 1,000 acres along the slopes of Lenox Mountain. For an easy hike of about one hour, take the Yokun/Beaver Lodge Trails Loop. You might see some beaver activity along the way. Also, Olivia’s Overlook is a lovely hike with pretty views at the center of 734 acre Yokun Ridge reserve.If you’re up for a challenge, take the Trail of the Ledges/Overbrook Loop to the top of Lenox Mountain. After an 850-foot vertical climb, you’ll be rewarded with magnificent views of the Catskill Mountains and the Taconic Range.
For Hiking close to the house in Monterey check out this website and this website features 13 of the best hikes with beautiful views.
Water Activities
Lake Garfield in Monterey is considered one of the most beautiful lakes in the Berkshires, making the beach an excellent spot to take in the natural beauty of Western Massachusetts and it’s the lake you are looking at from almost every window in the house. There is a small town beach you can visit which is a popular swimming spot in the summer as residents gather at the sandy shore, relax on the grass, or utilize one of the many picnic tables for an outdoor lunch. There is a boat launch for kayaks as well if you wish to bring one.
Stockbridge Bowl is another beautiful body of water with gorgeous views to take in while Kayaking or Paddleboarding. Arcadian Shop provides rentals and a drop off service on the lake. Black Swan Inn in Lee, Ma, a bit closer to the house, also offers Boat & Kayak Rentals.
Rent a pontoon boat for 1⁄2 day and have fun motoring around Copake Lake. There are 2 rental marina’s Copake Lake Boat and Ski and Mickey’s Marina.
In Pittsfield there is a family run operation called Onota Boat Livery with Boat rentals, canoes/kayaks/motor/pontoons.
Crab Apple Whitewater has daily rafting and kayak trips on the dam controlled Deerfield River a little over an hour from the house.
Beartown State Park: This 12,000 acre forest is the perfect place to visit no matter the season. Swim, boat, or fish in Benedict Pond. In the winter, you can cross-country ski and snowmobile. Located in Monterey.
Explore the Gilded Era Homes
The Berkshires was once a prime spot for the Gilded Age wealthy from New York and Boston to vacation – and continues to be a year-round destination. Slow down and take a stroll through one or more of the historic properties in the region. Notable writers, artists and entrepreneurs called these lavish properties home, but now the rest of us get to enjoy their Gilded Age beauty. There’s the Naumkeag, a 44-room Gilded Age “cottage,” a public garden and historic home in the heart of the Berkshires, Massachusetts, a 48-acre architectural masterpiece and Chesterwood, the former home to sculptor Daniel Chester French both have lovely outdoor spaces and often host arts and culture events. Fans of Edith Wharton can’t miss a free visit to the grounds at The Mount. (Pro tip: pack a picnic!) The mount (Edith Warton home & events) and the Ventfort Hall Mansion and Gilded Age Museum is a historic, Jacobean-style mansion and museum. The Blantyre, a Tudor Revival mansion on a 220-acre estate, is now luxury Hotel & Spa reopening in the Winter of 2024. Also included on the list is Bellefontaine Mansion now (Canyon Ranch) and the Wyndhurst and Coldbrook now the Miraval resort which is one of the most strikingly situated of the Berkshires Gilded Age mansions, located on a hill on Route 20, emerging like a castle to all those who drive by.
Are you ready for a getaway?
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Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.
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