Old Covered Bridge (Upper Sheffield Covered Bridge)

The Old Covered Bridge in Sheffield, also known as the Upper Sheffield or Sheffield Bridge, dates its story back to 1837-1838, when it was first built on a Town lattice truss across the Housatonic River. It was widened and rebuilt in 1854, and by the time the 20th century arrived it had earned recognition as the oldest covered bridge still standing in Massachusetts, added to the National Register of Historic Places in 1978.

That distinction ended abruptly in the early morning of August 13, 1994, when local teenagers set the historic bridge on fire and it burned to the ground — an act investigators ruled arson. Rather than lose the crossing entirely, the town rebuilt the bridge as a faithful replica of the original, completed in 1996 (some sources cite a final restoration date as late as 1998-99). It rests on granite abutments, one dating to the 19th century, the other rebuilt during a 20th-century rehabilitation, and runs 93 feet across the Housatonic on Covered Bridge Lane — a near-exact echo of the bridge that stood there for over 150 years before the fire.