Western Massachusetts community offering rural tranquility since the 1700s
Bordering Connecticut and about 9 miles from the New York state line lies the rural community of Sheffield. Here in southwest Massachusetts, locals can expect peace, quiet and hikers traversing the Appalachian Trail. Within the Berkshires, Sheffield sits amongst the rolling green hills and winding creeks of the Housatonic River Valley. “I really enjoy going to Sheffield, it’s so quaint,” says Elizabeth Nelson, Director of Marketing for 1Berkshire who relocated to the Berkshires from New York City. “There are beautiful old homes, farmhouses, woods and vistas.”
Sparsely populated and tucked into the Taconic Mountains, Sheffield’s remoteness is part of its charm. Country roads wind through the woods and past farmland; though they’ve been repaved over the years, some have been in use since the founding of the country. Sheffield is the oldest community in Berkshire County, which encompasses all of western Massachusetts. Sheffield was the site of the last battle of Shays’ Rebellion, a post-Revolutionary War uprising against the newly formed state government in 1787. Though it might seem like a simple stop along U.S. Route 7, historic Sheffield is a gateway for outdoor adventuring in southern Berkshire County.
Four-season outdoor recreation in the Berkshires
Between the ski areas, nature preserves and hiking trails, there is no shortage of outdoor recreation in and around Sheffield. The community borders Mount Washington State Forest, a 4,600-acre protected wilderness full of hardwood trees and hiking trails in the Taconic Mountains. Catamount Mountain Resort on the New York border is a small independent ski area, and Ski Butternut has a terrain park and tubing hill in addition to ski slopes. Ski Butternut produces artificial snow as needed, though the region does get snow and ice in the winter.
Hikers can explore Race Brook Falls, a moderately difficult trail leading to water cascading over rocks and fallen logs. Notably, the Appalachian Trail cuts across Sheffield. It is accessible at several points as it winds through forests, fields and along the Housatonic River. Hikers can expect flowers lining the hiking trails in the spring and a chance of ticks during warm weather.
Sheffield Town Park has Little League fields, a basketball court and a covered pavilion suited to large gatherings. In the center of Sheffield, Bushnell-Sage Library has a playground and a wildflower garden in addition to a robust library. Beyond books and media, patrons can also borrow ukuleles, board games and an all-terrain wheelchair.
The architectural designs of Sheffield span centuries
The residential landscape of Sheffield encompasses over 250 years of home designs; some are preserved from before the Revolutionary War. All are set on spacious lots offering privacy, tree cover and grassy lawns. Cape Cod, ranch-style and contemporary homes built between the 1760s and the 2020s sell at varying price points. Prices start at the low $200,000s, with some fixer uppers below that. The median single-family home price is $550,000. Homes peak in the low millions: secluded properties with panoramic mountain views, lush landscaping and spacious interiors up to 3,000 square feet range from $1 to $2 million.
Sheffield students attend Southern Berkshire Public Schools
Southern Berkshire Public Schools, including Undermountain Elementary and Mount Everett Jr./Sr. High School, are rated B overall on Niche. All Mount Everett students are automatically enrolled in the early college program; this partnership with Bard College at Simon’s Rock was the first early college program in the country. Alternatively, Berkshire School is a highly regarded, private boarding school. This co-ed high school is rated A-plus on Niche.
Local watering holes and farm-to-table dining in the Berkshires
The Marketplace Kitchen and Café is a chain unique to the Berkshires – kickstarting the farm-to-table trend in the region – serving espresso drinks, breakfast sandwiches and fresh salads. The Stagecoach Tavern at Race Brook Lodge feels like stepping back in time: though the 18th-century tavern is closing, the attached lodge regularly hosts live music shows, keeping the creative spirit of the Berkshires alive and thriving. At Sheffield Farmers Market, customers can shop for food, flowers and art while listening to live music. It is open year-round. Locally owned businesses like Big Elm Brewing and Berkshire Mountain Distillers line Route 7, along with antique stores and a Dollar General. More grocers can be found in Great Barrington. “Sheffield is close to Great Barrington, so [it’s got] great access to south county fun, restaurants and activities like the Mahaiwe Performing Arts Center,” Nelson adds.
Conveniently positioned along U.S. Route 7
Sheffield sits along U.S. Route 7, the only highway that runs north-south through the entirety of the Berkshires. Though Sheffield is not far from other hillside communities, the drive to the nearest metropolitan area – whether it be Springfield, Hartford or Albany – is at least an hour. Sheffield is 60 miles west of Springfield, and Bradley International Airport in Connecticut is about 50 miles southeast. Fairview Hospital is much closer in the neighboring town of Great Barrington.
A curious incident at the Historic Upper Sheffield Covered Bridge
One of Sheffield’s most unique features is that it’s the site of the first UFO encounter in the country to be verified by the government. On the night of September 1,1969, the Reed family encountered an unidentified flying object while driving near the Historic Upper Sheffield Covered Bridge – a UFO allegedly witnessed by 250 locals. A commemorative plaque by the bridge acknowledges the encounter, signed by Massachusetts Governor Charlie Baker. The site has been featured on the Netflix series Unsolved Mysteries.
