The Middle Covered Bridge in Woodstock was built in 1969 replacing an iron bridge that had been in use since 1877. The Middle Covered Bridge was constructed following traditional methods. Wooden pegs were used instead of nails, and the bridge was built on dry land and then pulled across the river on scaffolding drawn by oxen walking a capstan. With every turn of the capstan the bridge was pulled 3 1/3 inches closer to its final destination
On May 11, 1974, the bridge was set afire by arsonists. It took three years, and almost $55,000 to complete the required repairs.
In addition to the Middle Covered Bridge in the village, Woodstock has two other covered bridges, which are located in the hamlets of Taftsville and West Woodstock. The Taftsville Covered Bridge was severely damaged in 2011 by Tropical Storm Irene. After extensive renovations it reopened in 2013.