Garrison
Trail Running Calendar near Garrison 2026-2027
Explore the top trail runs near Garrison for 2026-2027! We've gathered 39 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Multi-distance trail festival at Ringwood State Park Sept 18–20 2026 with looped courses, a central aid station, and options from a kids mile to 100 miles.
Timed trail festival in Pawling, NY on Sept 19 to 20, 2026 offering 24 hour, 12 hour, 6 hour and 3 hour loop races with aid stations and finisher medals.
Looped trail ultra in Upper Nyack offering 50-mile and 27-mile options with significant elevation gain and three on-course aid stations.
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
October 2026
Four miles of trail running through the Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus on October 4, 2026.
A 13.7 mile trail race with 4,000 ft of gain in Cold Spring NY on October 4, 2026, listed as a UTMB Index Race; a portion of proceeds benefits the NYNJTC.
Trail run at Jungle Habitat in West Milford NJ with Half Marathon plus, 10K plus and 5K plus loops on a USATF sanctioned course featuring single track and fire road.
A timed 5K and accessible short run and walk at private Gemstone Farm in Wilton, CT with race shirt, post-race food, music, and support for The Prospector's mission.
A scenic 5K through the carriage roads of Rockefeller State Park Preserve with hilly terrain, Swan Lake views, awards, t shirts and 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.
A technical trail half marathon and 10K through Harriman State Park near Tuxedo NY, featuring steep climbs, rock fields, and significant elevation gain.
Trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a 5 mile race and two kids races, with Farm Bucks and kids medals.
Trail half marathon, 5K and a 3/4 mile kids run in Garrison NY, fundraising for The Friends of Philipstown Recreation with a course that passes Osborn Castle.
Tri-State New York Spartan Weekend in New Hampton, NY, Oct 31 to Nov 1, 2026 features Sprint and Super obstacle races, kids events, workshops and Hurricane Heat formats.
Trail running event in Lagrangeville, NY featuring 100k, 50k and 10k loop races with aid stations, finisher medals, awards and UTMB Index designation.
November 2026
Timed trail running on a 4 mile loop at Gurski Farm in Brookfield CT with 8 hour and 4 hour options plus a new 5K Canicross for 2026.
Trail events at Ward Pound Ridge Reservation: a 10k trail race on November 8, 2026 and a month long Raven 100k Challenge with wooden finisher medallions.