Dickens first served as a supply point in the late 1800s for cowboys living in line camps and working the surrounding historic ranches including the Matador, the Pitchfork, and the Spur. The community, named after Alamo defender J. Dickens, remained sparsely populated despite its position as justice center for the region. The Dickens County Courthouse, constructed in 1893, is now listed on the National Register of Historic Places. The two-story Romanesque Revival structure, built of locally quarried stone, once featured a central tower with a domed cupola (removed in 1936) and continues to serve the county today.

Dickens’ frontier cowboy history provided an appropriate place for its most recognized citizen, the late Charles Weldon “Tooter” Cannon, who relocated his “Tooter Cannon Saddles” operation to Dickens in the late 1960s. Tooter Cannon saddles, hand-made and designed to last generations, were sought after by both working cowboys and rodeo performers for their unique fit, designed specifically to adhere to the contours of the horse. Today, an exhibit on the life of “Tooter”, saddlemaker and former two-term member of the Dickens town council, can be viewed at the National Ranching Heritage Center in Lubbock.

The historic Dickens County Springs Park is located alongside US 82, and in nearby Spur visitors will find the Spur–Dickens County Museum, with exhibits tracing the region's rich ranching heritage and other aspects of frontier life.