Scenic and sophisticated, Sheffield lies in the Housatonic River valley, between Mount Everett (part of the Taconic Range) and Mount Washington, along the southern border of the Berkshires and Litchfield County, Connecticut. Sheffield is the oldest town in Berkshire County, having been settled in 1724 and incorporated in 1733. This town, which is made up of the villages of Sheffield and Ashley Falls, takes great pride in its rich historical character and arts-minded community. It’s also one of the best spots to hunt for antiques in the Berkshires, with its dozens of shops and hundreds of treasures to choose from.
The Appalachian Trail crosses through the northern part of Sheffield, while Route 7 intersects it almost down the center, creating easy access to the many attractions of Central and Southern Berkshire County, especially Great Barrington. It’s also one of the most beautiful drives in the region, with a profusion of greenery and flowers in the spring and summer and stunning displays of colorful leaves in the fall. With its proximity to New York City—it’s just a 2.5-hour drive—Sheffield is a favorite of second-home owners who maintain businesses in the city, as well as visual and performing artists.
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