Garrison
Trail Running Calendar near Garrison 2026-2027
Explore the top trail runs near Garrison for 2026-2027! We've gathered 30 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Timed laps at New Canaan High School Track where adults run for 14 minutes and 48 seconds and kids run one 400 m lap, with proceeds supporting the Ram Council Foundation.
An eleventh annual trail event at Ward Pound Ridge Reservation on Nov 8, 2026 featuring a 10k course to Raven Rocks Overlook and a November 100k virtual challenge.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
A community Turkey Trot at Sargent Elementary in Beacon NY with a 5K Run Walk, a one mile kids fun run, a food drive, live DJ and refreshments.
A memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
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.
Community Thanksgiving event at Somers High School with a 5K and 1-mile fun run, shirts, medals, age-group awards, and scheduled packet pickup days.
A 5K trail race at Stillwell Woods Preserve in Woodbury supporting The Center for Developmental Disabilities and held in memory of a community runner.
December 2026
Third annual 5K Reindeer Run/Walk on the Joel Barlow cross-country course in Redding, CT with festive attire encouraged and proceeds to the Class of 2029.
A 5 mile winter trail race at Mountain Lakes Park in North Salem NY with start and finish in the Yurt Village, a central firepit, and proceeds supporting park trail projects.
February 2027
April 2027
Mountain 10K and half marathon in Bear Mountain NY on rugged technical trails with steep climbs, scrambling, and mandatory safety gear.
A community trail event in Cross River, NY featuring a 5k trail race, a 4k walk on the same trails, and a 200 meter kids dash on the contest track.
Youth trail run at Katonah Memorial Park for ages 4 to 16 with 0.5 mile and 1 mile options; registration opens January 31, 2027.
A spring trail event in Cross River NY, Leatherman's Loop is a 10K lottery-entry race with a $58 fee that includes park entry.
May 2027
A technical trail race in Beacon NY with a half and full marathon featuring heavy elevation gain, exposed climbs, aid stations, and strict aid station support rules.
A technical mountain trail race in northern New Jersey offering a 50K with over 7000 ft gain plus 10 mile and 5 mile options, map requirements for the 50K, mandatory gear checks, and aid stations on the longer courses.