The Thomas Jefferson Parkway was developed by the Thomas Jefferson Foundation to create a scenic entrance along Route 53 to Monticello. The Parkway also serves as a recreational and educational resource for visitors and as a pedestrian and cycling link between Monticello and the local community. Along the Parkway, four miles of utility lines were buried, guardrails were removed when possible, and the road shoulders were landscaped. 

At the base of the Parkway along Route 53, Kemper Park includes an arboretum of native trees and shrubs, Carter Overlook, a two-acre pond, and a small trailhead parking lot. A 2-mile trail, Saunders-Monticello Trail, also winds through the park before ascending the side of Carter Mountain toward Monticello. The trail then leads directly to the Monticello ticket office over the recently completed stone-arch Saunders Bridge. A pedestrian underpass at the lower trailhead that leads to additional parking will constitute the final piece of the project. 

The Parkway was designed by the Charlottesville landscape architecture firm Rieley and Associates and built by another local firm, Abrahamse and Co. A combination of public and private funding supported the project. Federal highway grants from the ISTEA (Intermodal Surface Transportation Efficiency Act) program totaled $3.4 million, while private donations provided $3.1 million. Among the donors were Mr. and Mrs. Thomas A. Saunders III, the Crosby Kemper family of Kansas City, the Robert Carter family, the Perry Foundation, State Farm Companies, Sprint Corporation, Dominion Virginia Power, the Helmerich Foundation, the Richard Gwathmey and Caroline T. Gwathmey Memorial Trust, and numerous local garden clubs.

Construction began in 1996. By 1998 a majority of the landscaping and trail building was complete. The Parkway's arboretum and trails opened to visitors in 2000. The Thomas Jefferson Parkway, Kemper Park, the Saunders-Monticello Trail, and Saunders Bridge were dedicated in a public ceremony on Saturday morning, November 2, 2002.