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The Berkshires: Where Culture Meets Canine

From posh pet digs to extraordinary art spaces, there is plenty of dog-friendly summer fun to be had.

by Matthew Wexler
July 10, 2021
A dog standing on a green hill overlooking a double rainbow on a blue sky
Hakan & Sophie / Stocksy
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Gilded Age glory reigns supreme in the Berkshires, where western Massachusetts’s postcard-perfect towns and rolling hills harken back to 19th-century opulence. Today a backdrop for a new generation of forward-thinking artists and tastemakers, the region has long provided respite for dog lovers, including novelist Edith Wharton  (The Age of Innocence, House of Mirth), whose lush, 100-plus-acre Lenox estate gave her beloved dogs Mimi, Miza and Jules plenty of room to roam in the early 1900s. The Berkshires has embraced its dog-centered culture and is an ideal dog-friendly travel spot.

Berkshire County encompasses more than 900 square miles, but the winding two-lane roads make for long travel times between destinations, so it’s best to plan strategically to ensure that time is well spent.

North County

On the west is the Clark Art Institute, a pastoral 140-acre campus that houses a public art museum designed by Pritzker Prize-winning architect Tadao Ando and a research center as well as dog-friendly walking trails.

A quintessential Berkshires meal can be had at nearby Mezze Bistro + Bar, overlooking Williamstown’s Sheep Hill. Chef Nicholas Moulton oversees the seasonal menu, which draws from the bounty of local farmers, while signature cocktails rely on handcrafted artisan spirits from Berkshire Mountain Distillers.

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No trip to the Berkshires is complete without a scenic outdoor adventure. Leashed dogs are permitted on the Ashuwillticook Rail Trail an 11-mile converted rail line, which offers plenty of spots for picnics and sightseeing. Mount Greylock State Reservation has trails with various degrees of difficulty culminating at the 3,500-foot summit. Pets must be leashed at all times.

At day’s end, pet-friendly Porches Inn provides accommodations in lovingly restored Victorian row houses decorated with retro furniture and vintage accents. Crates are available if needed, and each four-legged guest receives biscuits and a personalized welcome letter from Sabine, the house cat.

South County

Head south on Route 7, where more adventures await, including Turn Park Art Space, a pet-friendly outdoor art park on the site of a former quarry. Co-founders Igor Gomberg and Katya Brezgunova have reimagined the 16-acre space with exceptional work from artists across the country, along with community events all summer long. Dogs are welcome on leash.

Coffee culture reigns supreme in the Berkshires, and one of the most coveted cups can be found at No. Six Depot, just a short stroll from Turn Park. Sustainably grown organic beans are hand-roasted in-house in a vintage Probatino roaster; try their signature Berkshire Sky, a blend of Sumatra Ketiara and Ethiopian Yirgacheffe. On-leash pets are allowed on the café’s outdoor patio.

The Berkshires is also home to nearly a dozen craft breweries and cideries, including solar-powered Barrington Brewery & Restaurant, where beer lovers and their leashed dogs can enjoy Berkshire Blonde, Raspberry Ale and other seasonal brews on the outdoor patio.

For posh pet digs that embody the Berkshires’ luxury lineage, Annie Selke’s 33 Main in Lenox dates back to 1836 and has been meticulously refurbished by the renowned designer. Opt for the Aster (one of two dog-friendly rooms), which features a crisp white-and-royal blue palette, a soaking tub, homemade dog treats, and a special bed for traveling canines.

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Matthew Wexler

Matthew Wexler

Matthew Wexler is a nationally recognized travel and lifestyle writer whose work has appeared in more than 20 publications and online media outlets. He is also the proud parent of Luey, a rescue dog from Rescue Dogs Rock NYC.