Human habitation in the Sherwood area is very ancient as evidenced by the many thousands of Native American projectile points in the nearby fields.

It is located on an old Stagecoach route approximately midway between Sewanee and Anderson, Alabama and is representative of the hamlets and villages that were once commonplace in the area coves and valleys.

Named for station master Meridith Catchings, the small community began appearing on railroad maps after the Civil War.

[13] A number of sources have erroneously reported that Charles Sherwood was lieutenant governor of Wisconsin and that the town was established in 1875.

[15] With the construction of the strategically important Cowan Tunnel 5 miles (8.0 km) to the north in 1852, train stops were created through the Crow Creek Valley, including at Catchings Station (Sherwood).

Notably, at this station there were and continue to be pusher engines which are required to assist with train ascents up the steep mountain grade to the tunnel.

[17][18] As of the 1930 census, Sherwood had 1,700 residents, but the community's population declined to 900 in the 1950s as its economy stalled after the closing of the limestone plant.

[21] In 1956, the mission helped train a group of women and opened a shirt factory in Sherwood in an attempt to create local jobs.