If you’re longing to escape to an 18th-century village full of historic sites, charming shops, and lush landscapes dotted with covered bridges, the Berkshires region is a particularly ideal place to explore. Home to small but mighty mountain towns like Stockbridge, Massachusetts, and glam roadside hotels, the region is positively brimming with quaint destinations.
Nestled near the border of Massachusetts and Connecticut, is Berkshire County’s oldest town, Sheffield. Dating back to 1733, the small town is home to around 3,200 residents and well-populated with historic landmarks, seven of which can be explored at the Sheffield Historical Society. There are also unique opportunities to visit quirky attractions like the Thom Reed UFO Park and outdoor art displays at the Butler Sculpture Park. With an abundance of forest-lined trails for hiking adventures in the beautiful Berkshires and a treasure trove of antique shops for vintage shopping sprees in town, Sheffield is the perfect spot for your next New England getaway.
Historic attractions in Sheffield
Some of Sheffield’s main charms are its historic sites. To dive straight into the town’s roots, the Sheffield Historical Society campus is the best place to start. Located on Main Street in the heart of town, the property boasts seven 19th-century structures, including a carriage house, an 1820 law office, and a Greek Revival-style smokehouse. Tucked inside the 1834 Old Stone Store, you’ll find a small gift shop and gallery open on the weekends from May through October. The site’s focal point is the 1774 Dan Raymond House, which contains the Historical Society’s main office, as well as a museum. You’re free to wander the grounds daily during the day. To schedule a tour of the museum in advance, contact the Sheffield Historical Society by phone or email.
About 4 miles south of the Sheffield Historical Society, you’ll find another historic site, the Ashley House. Built by Colonel John Ashley in 1735, it is the oldest home in Berkshire County and one of the first European-style homes built in the region. The home is known for its significant ties to the end of slavery in Massachusetts, as one of its enslaved occupants, Elizabeth Freeman, sued Ashley for her emancipation (and won) in 1781. The grounds are open to explore daily, while the Elizabeth Freeman Exhibit inside the house is open seasonally from sunrise to sunset.
Unique parks and antique shops in Sheffield
To discover an attraction that’s out of this world, visit the Thom Reed UFO Park. Situated along the Housatonic River in Sheffield, the public park consists of a blue covered bridge marking the site of a famous sighting in 1969. According to eyewitness Thom Reed, who was 9 years old at the time, he and his family had a very close encounter with a UFO while driving through the bridge one night, which manifested in a mysterious orb of light and a shell-shaped disc hovering in the air. Whether you believe in aliens or not, the tiny park is a fascinating spot and a legendary part of the town’s past…