Thomas Jefferson Parkway, Monticello’s entrance corridor along Route 53, features a 175-mile park with a large pond, woodland amphitheater, native plant arboretum, overlook, and accessible trail for pedestrians and bicyclists. As the 2.2-mile trail traverses through woods and over streams, great care was taken to delicately weave the 10-foot wide trail through the mountain’s formidably steep slopes while disturbing as little of the natural surroundings as possible.

A stone arch bridge carries vehicular and pedestrian traffic safely over Route 53 and onto the Monticello grounds. The bridge is reminiscent of the Pont de Neuilly, admired by Jefferson during his stay in Paris, and reflects an 18th century aesthetic down to the stone barrel vault. Completed in the spring of 2000, the Thomas Jefferson Parkway remains the area’s most popular park. It received the 2016 Virginia Landmark Award for design of a historic landmark. The walkway connecting Monticello and Kemper Park was also designated a Community Millennium Trail by the White House Millennium Council in 2000.