Darien
Trail Running Calendar near Darien 2026-2027
Explore the top trail runs near Darien for 2026-2027! We've gathered 51 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail races at Tarrywile Park in Danbury offering Marathon, Half Marathon and 10K on a loop course with technical single-track, substantial elevation gain, and cupless aid stations.
A scored cross country 5K at Van Cortlandt Park on November 15, 2026, open to ages 8 and up, run on wooded trails with on-site awards and race-day amenities.
Six hour run and relay at Belmont Lake State Park on November 15, 2026, honoring Fred von der Heydt with individual and 4 and 6 person team options.
A trail half marathon at Roosevelt Forest on November 21, 2026 featuring eight 1.64 mile loops, on-course aid, commemorative swag, and podium awards for top male and female finishers.
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 community 5K at Inwood Hill Park on November 26, 2026, with proceeds to the Inwood Food Pantry, personalized bibs by 11/1, and medals for the first 700 finishers.
A community 5K run/walk and 1/2 mile fun run at John J Burns Park on November 26, 2026 supporting local charities with awards and refreshments.
A community 5K run and virtual option at Alley Pond Park on November 26, with a free kiddie dash, on-course refreshments, and proceeds supporting the Never Stop Running Foundation.
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.
Charity 5K and timed 1 mile walk/run at Darien High School on November 27, 2026 supporting The Depot, with family activities and bib pickup options.
5K trail run and virtual 5K at Bethpage State Park on November 28, 2026 with a free kiddie dash and proceeds supporting the Never Stop Running Foundation.
A revived 9 mile cross-country race in Van Cortlandt Park covering three loops of the park’s XC course with awards, commemorative buffs, and a post-race pub gathering.
A 5K trail race at Stillwell Woods Preserve in Woodbury supporting The Center for Developmental Disabilities and held in memory of a community runner.
A trail 5K at Belmont Lake State Park on November 29, 2026 where no traditional awards are given but a cash raffle returns 50% of net proceeds to participants.
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 trail only 8K at Sunken Meadow State Park in Kings Park, NY on December 6, 2026, with a post-race raffle and holiday cookie fest; proceeds support local charities.
A backyard ultra at Blydenburgh County Park: runners repeat a 4.167 mile loop each hour until one completes the final loop; proceeds support Long Island trail maintenance.
A 5 km park race at Van Cortlandt Park on December 12, 2026, presented by Race The Bronx and Cash Cow NYC with race T shirts and bag check.
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.