Pawling
Trail Running Calendar near Pawling 2026-2027
Explore the top trail runs near Pawling 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.
October 2026
Trail races at Mohawk Mountain Ski Area in Cornwall, CT on October 11 with 5K, 10K, half and full marathon courses over ski slopes and Mohawk State Forest.
A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.
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.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
Trail half marathon and 5K in the Hudson Highlands with a kids costume run and aid stations for the half.
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.
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.
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
A 100 percent cross country 5K at White Memorial Foundation & Conservation Center in Litchfield with natural trail footing, a midcourse hill, on-site outhouses, and Sawmill Field parking.
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 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.
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
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
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.
April 2027
Mountain trail races at Bear Mountain on April 3, 2027 offering 13.1 mile, 10K and 10K ruck on rugged technical singletrack with significant elevation gain.
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.