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.
Test your endurance at the Pawling 24 Hour Trail Running Festival featuring multiple timed races on a scenic 1.68 mile loop in Lakeside Park.
Experience a challenging 50 mile or marathon trail race featuring 9600 feet of elevation gain and scenic Hudson River views at Hook Mountain.
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.
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 loops at Jungle Habitat in West Milford, NJ, offering Half Marathon+, 10K+, and 5K+ courses with marked single track, cupless aid stations, and RideWithGPS maps.
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.
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.
A community half marathon, 5K and kids fun run in Garrison, NY, with trails through Hudson Highlands and proceeds benefiting local recreation programs.
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.
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.