Prospect
Trail Running Calendar near Prospect 2026-2027
Explore the top trail runs near Prospect for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
On October 24, 2026, the New Hope Wesleyan Ultra Trail Run offers four trail distances at O'Bannon Woods State Park, featuring single-track forest trails, rocky sections, notable elevation changes, aid stations, timing, and awards for top finishers.
November 2026
A chip timed 5k run/walk at Turtle Run Winery with race swag and a wine pour at the finish, supporting Special Olympics Indiana Harrison County.
A 5K and Half Marathon at Active Heroes Retreat in Shepherdsville, KY on wooded trails and gravel roads supporting military members and veterans.
Nov 8, 2026 in Borden IN features 6 hour and 12 hour trail endurance races plus a one lap fun run on a 4.167 mile loop with steep climbs and creek crossings.
Trail half marathon at Jefferson Memorial Forest on November 21, 2026 featuring hilly trails, aid stations at miles 2 5 8 and 11, and registration deferral instead of refunds.
December 2026
Experience an exclusive trail event at the Harry S. Frazier Scout Reservation featuring looping courses through Kentucky forest and a runner's village by John Barr Lake with distances from 5K up to 100 miles.
Trail races at Waverly Park offering a roughly 6 to 6.5 mile loop and a half marathon, with on-site packet pick-up, an aid station, and a virtual option.
January 2027
Trail running event in Simpsonville KY with a 4 mile loop and an 8 mile double-loop across grass, singletrack, cedar rows and creek crossings.
Nine mile trail race at Jefferson Memorial Forest near Horine, part of the Winter Warrior Series; cupless event with an aid station, finisher coin, and optional shirt.
February 2027
April 2027
A rugged point-to-point 50-mile trail race on Indiana’s Knobstone Trail with roughly 10,000 ft of elevation gain, multiple aid stations, drop-bag support, and cupless water service.