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The Homestead Trail winds its way through Colorado Springs, intersecting with some of the area's most prominent trails as it goes. The trail currently exists in two close but disconnected pieces. The northern segment runs from Templeton Gap, through Fred McKown Park & Field and up to Cottonwood Creek Trail.
The second segment is abuot twice as long and starts on the Stetson Trail. This is a good point to start your journey give the parking at the High Chaparral Open Space Trailhead. The Homestead Trail doesn't go into the High Chaparral Open Space itself though. Instead it winds south , through Old Farm Park. From there it continues its serpentine course, meandering south and then west between houses, near schools and through even more parks.
This trail meets Colorado's Rock Island Trail at Constitution Avenue. From there the final stretch of trail sits on the east side of a canal down to Galley Road.
You can park at the High Chaparral Open Space Trailhead off Stetson Hills Boulevard west of Austin Bluffs Parkway. Additional parking is available at the parks along the route of the Homestead Trail.
The condition of this trail is terrible. Tree roots have buckled the pavement. There are large potholes throughout making it very dangerous to ride on. It is clear that the city has never made an investment to repair the damages. Do not use this trail.
Terrible for anything other than walking and even that would be strenuous. HUGE gaps in the pavement ever 10-15 feet
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