Sheffield

Sheffield, Massachusetts

If you’re driving into the Berkshires from the New York metropolitan area, there’s a good chance that you’ll find yourself passing through the small town of Sheffield once you cross into Massachusetts. And while this small town may not seem worth checking out, Sheffield has a lot more to offer than you might think!

Nestled right at the Connecticut border on the banks of the Housatonic River, Sheffield is another picturesque New England town. The surrounding area of the southern Berkshires offers an abundance of outdoor recreation, including Mt Washington State Forest and Bartholomew’s Cobble Reservation.

The reservation is exceptionally rich in biodiversity, with over 250 species of birds and over 800 species of plants having been documented. Explore the area with 5 miles of trails and take in the natural beauty as you cross through fields, forests, marshes, hills, and more. There are even several small caves on the reservation, making it a great place to spend the day with the whole family!

Back in town though, one of the best things to do in Sheffield is antiquing, and the town boasts an impressive number of antique shops with 5 of them up and down Main Street. Le Trianon is regarded as one of the best with museum quality art and pieces, and it’s been praised several times by Architectural Digest, Town & Country, and even the New York Times!

If you’re more in the mood to browse and wander around though, head out to Butler Sculpture Garden on Shunpike Road. There, you’ll find over seven acres of winding paths and open exhibition areas with hundreds of stainless steel sculptures crafted by a single artist. 

Now, if this type of cultural activity isn’t quite your thing, you may want to pay a visit to the Berkshire Mountains Distillers. The distillery produces an assortment of spirits, ranging from vodka and gin to aged rum and bourbon whiskey. In fact, their Greylock Gin is a San Francisco Spirits Competition gold medal winner, and has been called the country’s number one craft gin by the New York Times!

Sheffield may be a small town that’s easy to overlook, but it’s absolutely full of hidden gems and well kept secrets. If you have the time on your Berkshires visit, take a trip down for the day…you just might be pleasantly surprised as to how much this cozy little town has to offer!