The Woodstock Academy Classroom Building is a historic school building on Academy Road in the Woodstock Hill village of Woodstock, Connecticut. Built in 1873, it is the oldest standing building on the campus of the Woodstock Academy, which was founded in 1801. It is a three story wood frame structure stands impressively overlooking the Woodstock Green. It is nine bays wide, with the middle three projecting outward. The building is capped by a two-stage belltower. It was built after a fundraising campaign by New York businessman Henry C. Bowen, whose summer residence, the Roseland Cottage, also faces the green.