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Activity Level: M
Start / Finish: Boston / New York
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The Road Not Taken
The Berkshires are where art and nature collide—a veritable playground of hallowed cultural institutions, historic homes, picture-postcard hamlets and mile after mile of top-shelf biking. Accessibly out-of-the-way this is mythic small-town New England in the flesh. We could go on forever about the marvelous backcountry biking, but then we’d neglect everything else: the first-rate museums and art galleries (including the Massachusetts Museum of Modern Art, open at night just for us); the cozy villages and college towns (which we’ll ride through); Litchfield Hills’ award-winning wines (we’ll taste them); and the truly stunning hotels like the see-it-to-believe-it Winvian, exclusive to B&R. Experience the Berkshires with us: it’s not just for fall foliage.
Here’s a sample of what you can expect on your custom-designed Bespoke Berkshires adventure. Intrigued? Contact a Bespoke Trip Planner for further details.
Day 1 Savour a private tour of the Massachusetts Museum of Contemporary Art, the largest modern-art gallery space in the United States
Day 2 Take our “Tri-State Ride”—67 km of brilliant riding through Massachusetts, New York and Vermont before spending the afternoon in quaint Williamstown
Day 3 Bike the historic Ashuwillticook Rail Trail, a former railway line turned cycling haven and chat with local historian Carol Owens
Day 4 Visit the Norman Rockwell Museum and the historic homes of cultural icons Edith Wharton and Daniel Chester French
Day 5 Lunch at an award-winning winery before spending the night at the Winvian, easily the world’s most unique luxury hotel—and exclusive to B&R
Day 6 Breakfast in Morris, CT, and farewells in New York
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The Porches Inn at MASS MoCA, North Adams
This cleverly renovated string of Victorian row houses makes for an unusual and stylish hotel experience. The rooms feature luxurious linens and modern amenities alongside such quirky design features as paint-by-number art, ’50s-era lamps and salvaged building materials. Facilities include a gym, a small heated pool, a sauna and a Jacuzzi.
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Wheatleigh, Lenox
Modeled in the style of a 16thC Italian villa, Wheatleigh is about as elegant as it comes. Gorgeous grounds, stunning views and superb service. The hotel is located just two miles outside of Lenox and more or less around the corner from Tanglewood. The dining room has earned a surfeit of accolades for its outstanding menu and stellar service.
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Winvian, Morris
Set amidst 113 acres in the Litchfield Hills, Winvian is one of a kind. Fifteen different architects designed each of the 18 unique and whimsical cottage “rooms,” each conceived around a specific Connecticut theme. The state’s artistic legacy is honoured in “The Artist,” a painstaking recreation of a 1920s artist’s bungalow, while the majesty of the great outdoors is captured in the “Camping” and “Treehouse” cottages. “The Helicopter” is truth-in-advertising incarnate: a room built around a fully-restored Sikorsky Sea King Pelican helicopter. This is a place that simply has to be seen to be believed... and even that might not be proof enough.
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Moderate
This trip is rated Moderate. Daily riding distances range from 35 to 61 km (22 to 38 mi.), with options for shorter and longer rides on all days. The terrain is, for the most part, rolling with occasional hilly stretches and one 16 km (10 mi.) flat trail ride. All rides are on paved roads with one 3 km (2 mi.) exception on the third day.
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