Covered Bridge Lane leads to the historic Sheffield Covered Bridge. The bridge was built in 1832 and spans the Housatonic River, connecting Sheffield and New Marlborough. It is one of the oldest surviving covered bridges in the state and is listed on the National Register of Historic Places. The bridge is 93 feet long and 12 feet wide and has a wooden truss design. It was restored in 1998 and is open to pedestrians and bicycles. 

Covered Bridge Lane crosses and then parallels oxbows in the Housatonic River.