The Wilmington Trail Club began planning the Trail in 1941, shortly after the club was founded. Starting at Henry Clay, on the Brandywine River just south of the Hagley Museum , it was planned to follow the river valley north towards the Horseshoe Trail, which in its turn connects with the Appalachian Trail north of Harrisburg . Permission was obtained from landowners, including four members of the du Pont family, and H. G. Haskell, owner of Hill Girt Farm, Chadds Ford. Work commenced in 1942, and by 1948 the HT was reached near Bacton , PA , a distance of 28 miles. During the 1970s, the Chester County Trail Club took over maintenance of the trail north of Chadds Ford, and the upper section was rerouted to join the HT at Horseshoe Trail Road near Ludwig's Corner, PA, making a total distance of approximately 36 miles. In recent years, due to development at Rockland, access to the southernmost section has been lost, and the trail now crosses Rockland Bridge to terminate in Brandywine Creek State Park, on the west bank of the creek.
The trail is intended for exclusive use of members of the two maintaining clubs and their guests. The main use of the trail occurs in the late winter and early spring when preparatory warm-up hikes are held for the annual End-to-End hike in one day.
Early End-to-End hikes were informal affairs with the hikers using their own vehicles for car-pooling and carrying their own supplies. Around 1960, a few members decided to wait at the end with coffee and doughnuts for the hikers, and began the practice of recording finishing times. Since then the hike has evolved to its present day format, with bus shuttle, trail guides, refreshment checkpoints and sweeps. In past years, hikers clambering over the rocks opposite Hagley were cheered on from across the creek bank by the team at the final checkpoint near the entrance to the museum. Hikers preparing to ascend the final hill now enjoy a welcome from the team looking out from a vantage point at the Hawk Watch Pavilion in Brandywine Creek State Park, where a celebratory cookout is provided.