Trains belong to the Manassas Gap Railroad first arrived in Woodstock on August 27, 1856. The following year, a two stall engine house was constructed near this site. This structure would be destroyed during the Civil War.
In 1885 a depot was built by the B&O Railroad. It stood on the south side of Court Street and was later home to the freight office.
Three years later a new depot was built on what was called the “commons.” This was an ornate, limestone structure. It was more elaborate than most stations in the area, especially when one considers Woodstock’s modest size. A large covered platform stretched from the building to Court Street and facilitated the loading of passengers.
It served until 1948 when passenger service ended. In 1954 the structure was sold to Gordon “Sonny” Bowman who dismantled it and used the material to construct the press box at the Massanutten Military Academy’s football field.
Many locals passionately opposed the railroad’s decision to demolish the building and that its eventual loss damaged Woodstock’s historic character.