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The Monacan people called this land home until settlers began moving West, claiming and cultivating large tracts of riverside. As early as the 1770's, the parcel we refer to as the "Circus Grounds" was productive agricultural land, farmed by free and enslaved people for generations. 

The land was sold to residential developers in 1891, but as the country entered an economic depression, few lots were sold. Instead, the land was purchased by Henry Clay Merchant, the proprietor of the Woolen Mills, for use as pastureland. Clay's heirs leased and later sold this property to Albemarle Golf Club (where Fairway Avenue gets its name). In 1920, Paul Goodloe McIntire—the philanthropist responsible for McIntire Park and Market Street Park—attempted to buy the golf course property and donate it to the people of Charlottesville as a public park. Negotiations fell through and the golf course continued to operate in its location for seven more years, until merging with a new club in Farmington. 

At this time, the land was sold to John Wesley Bagby, a life-long employee of the Woolen Mill. Bagby's Show Grounds began hosting circuses and carnivals in the 1940s, a tradition that continued for half a century. The property was sold to its current owners over a series of purchases, from the 1960s to the 1980s. 

Since 2015, a portion of this land has been leased by Charlottesville's paddling outfitter and guide service, Rivanna River Company. In 2022, a preliminary site plan for the development of a 245-unit apartment complex and parking lot was submitted for review by the City. The most recent iteration of this plan, submitted in early 2023, adds two publicly-maintained roads, including one through the current Rivanna River Company site.