The Homestead Trail is about 7 miles in length, with a couple disconnects. The northern segment is about 2 miles long, it feeds off of the Cottonwood Creek Trail heading southeast, ending abruptly at Templeton Gap Rd, from there users can travel by sidewalk to the southern segment which begins at the High Chaparral Open Space Parking lot off Stetson Hills Blvd (accessible only when driving east on Stetson Hills).
This is the more commonly known portion of the Homestead Trail. It stretches for 5 miles, encountering several major street crossings and a handful of neighborhood parks. The Homestead Trail is not an easy ride, it has rolling hills and the trail surface ranges from dirt to concrete, but it is mostly asphalt (some sections are very rough and deteriorated). Homestead trail terminates at Radiant Dr.
This trail is managed by City of Colorado Springs Parks, Recreation and Cultural Services: (719) 385-5940. For more info visit coloradosprings.gov/parks.
Connections: Homestead Trail connects to Cottonwood Creek Trail, about a mile south of Woodmen Rd. The trail travels though or next to several parks including Old Farm, Rudy, Homestead, Villa Loma and Penrose. With some street/sidewalk use it is possible to access Palmer Park and the Rock Island Trail. Homestead share a trailhead/parking lot with High Chaparral Open Space.
Future Plans: Eventually Homestead Trail should connect to the Rock Island Trail. The gap between Templeton Rd and Stetson Hills Blvd will be connected with a new trail segment. View COS Park System Master Plan, which includes trail networks.