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 Largely located in Western Massachusetts, with parts spilling over into Vermont, New York, and Connecticut, the Berkshires is a region often referred to as the “Berkshire Hills.” The seclusion of its lakes and hills, along with its mild summers and brilliant autumns, have long drawn vacationers and artists to its midst.
In the late 19th century, the Berkshires earned the nickname “inland Newport,” thanks to affluent families from New York and Boston who built summer “cottages” in the region. With their philanthropic support, performing arts and cultural events sprouted up throughout the area.
By the 1930’s, theater, dance, and music performances had established themselves as regular summer fixtures. Prominent writers such as Edith Wharton, Nathaniel Hawthorne, and Herman Melville were among those to live and work in the region.
Today, such institutions as the Tanglewood Music Center in Lenox (summer home of the Boston Symphony Orchestra), Jacob’s Pillow (America’s longest-running dance festival), Shakespeare and Company (in Lenox), and the Berkshire and Williamstown Theater festivals draw tens of thousands of visitors every year. The plethora of live music, dance, and theater has turned the region into one of the culture capitals of New England.
Autumn in the Berkshires is a particularly spectacular time to visit. This is the most colorful season in New England, as maples, birches, beeches and oak trees lose their green, and turn into a rainbow of reds, oranges, yellows and purples.
With numerous trails, including parts of the Appalachian Trail, there are countless great hike options. Parks such as Kent Falls, the Berkshire Botanical Garden, and the Herbert Arboretum are all popular among nature lovers. Catch a glimpse of more brilliant fall foliage along the Housatonic River Valley, where the Berkshires extend into Northwestern Connecticut.
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 Property 100476
The Winthrop Estate
- Since the late nineteenth century, the Winthrop Estate has been the vacation estate for some of America’s most prominent families. Set on more than thirty acres in the heart of Lenox in the Berkshires, this gilded age mansion has been carefully restored.
- In the main bedrooms, the estate accommodates up to twelve people in grand fashion. These bedrooms are beautifully appointed with antique furniture and many have fireplaces.
- There is plenty of space for children to play. A ninety-foot verandah looks out over a five-acre lawn with a stunning view of Lenox Mountain. The grounds are ideal for outdoor games, hiking, cross-country skiing, and picnicking.
- Historic Lenox Village is a ten-minute walk and has shops and nice restaurants. Tanglewood is less than a five-minute drive and nearby attractions include Shakespeare and Company, the Clark Art Museum, Jacob’s Pillow Dance Festival, Hancock Shaker Village, and Norman Rockwell Museum.
- We can customize your stay by helping you to arrange a private chef, tickets to cultural events, croquet, horseback riding, golf, rowing, local hiking guides, access to a private fishing club and health club, a masseuse, baby sitter, music lessons or private concerts.
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 Dana Biberman, Property 112466
Pumpkin Picking Five Minutes Away!
- Secluded 3-bedroom cape style house
- On 2 wooded acres
- Fully equipped kitchen
- Wonderful fireplace
- Near hiking, antiquing, and more
- Spectacular fall foliage
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Julia Woogen, Property 31050
Pumpkin Picking Five Minutes Away!
 When I think of the Berkshires I think of unsurpassed natural beauty, the great outdoors, history, art, culture, and, of course, adventure.
- In the fall when the air is brisk, it’s such a pleasure to head down the road to the Green River Farm for some hot apple cider. The Green River Farm, located at the intersection of Rt. 7 and Rt. 43, is a working farm with a wonderful apple orchard, among other things.
- A short walk down the road from Jiminy is the Ioka Farm, which delights young, and old alike with their annual Pumpkin Patch. I would be remiss if I didn’t mention Jiminy’s “Fun Park” because it always brings out the child in me. I can’t possibly convey the thrill of riding “the mountain coaster” or the “alpine slide.”
- Come Fall, the oak, pine and maple trees make their statement by lighting up the hills with hues of brown, yellow and red. An absolutely indescribable experience is to drive or walk to the lookout point at Mt. Greylock.
- As Fall leaves the Berkshires, in comes mother nature with her blanket of pure white snow to delight skiers young and old. Anyone will tell you that Jiminy Peak is the premier, family-oriented ski resort in Massachusetts for skiers and snowboarders alike.
- Thanksgiving marks the beginning of the holiday ski season, and what better place to celebrate Thanksgiving than in New England - it’s birthplace. The air is filled with pumpkins, hay stacks, scarecrows, and the like to remind everyone of this heartwarming family holiday.
- In our well-equipped country kitchen you can prepare a holiday feast and gather around the fireplace to share stories. A dip in the hot tub completes your evening.
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