In the 18th century, Rocky Woods was common land that the Town of Medfield later divided into woodlots and parceled out to residents. They used sleds to haul out felled trees for cordwood and building timber. In the early 19th century, this network of logging roads was used to haul away high-grade slabs of granite that were quarried from a hillside west of Chickering Pond. Rocky Woods granite was reportedly used to build the 1825–26 Dedham Courthouse.
In the late 1920s, Dr. Joel Goldthwait began buying woodlots in Rocky Woods, which by then had little commercial value. He created riding and walking trails through some 300 acres of woodland, which he donated in 1942 to establish the Reservation.