Garrison
Trail Running Calendar near Garrison 2026-2027
Explore the top trail runs near Garrison for 2026-2027! We've gathered 36 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.
Experience 13.7 miles of Hudson Highlands trails with 4000 feet of elevation gain during the peak foliage season in Cold Spring New York
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.
Pickle themed Halloween obstacle event at Obstacle Wonderland in Wallkill NY with adult 5K, kids 1K, a pumpkin carry fundraiser, themed medals, and family friendly activities.
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.
Test your endurance at Red Wing Recreation Area with a series of looped trail races ranging from 10k to 100k featuring significant elevation gain and constant support.
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.