Garrison
Trail Running Calendar near Garrison 2026-2027
Explore the top trail runs near Garrison for 2026-2027! We've gathered 37 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
October 2026
A 4 miles trail race through Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus.
Trail half-marathon in Cold Spring, NY on October 4, 2026 covering 13.7 miles with 4,000 ft of climbing through the Hudson Highlands; proceeds help NYNJTC.
Trail races at Jungle Habitat in West Milford NJ featuring a 13.2 mile half, a 6.6 mile 10K plus loop, and a 3.4 mile 5K plus with cupless aid stations.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
Scenic 5K at Rockefeller State Park Preserve featuring hilly carriage roads, age group and team awards, t shirts and refreshments, with proceeds supporting carriage road maintenance.
A pickle themed Halloween obstacle event in Wallkill NY on October 11 2026 with a 5K adult course, 1K kids race, themed medals, and a pumpkin carry fundraiser.
HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.
Technical trail races in Harriman State Park featuring a rugged half marathon and a steep 10K with substantial elevation gain and marked singletrack.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
Trail and road 1/2 marathon, 5K, and kids 3/4 mile run in Garrison NY on October 25, 2026 supporting the Friends of Philipstown Recreation.
A Spartan obstacle-course weekend at Sunflower Valley Farm with Sprint, Super, Kids races, workshops, and Hurricane Heat events from Oct 31 to Nov 1 2026.
Trail ultramarathon weekend in Lagrangeville with 100k, 50k and 10k looped courses, UTMB Index status and continuous on-course aid.
November 2026
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
A community 5K and a 1-mile kids run at Sargent Elementary in Beacon, NY, with a food drive, live DJ, and refreshments.
A farm based 5K trail run plus a kids fun run for ages 6 and under in Yorktown Heights supporting Friends of Hilltop Hanover Farm.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.