Stamford
Trail Running Calendar near Stamford 2026-2027
Explore the top trail runs near Stamford for 2026-2027! We've gathered 58 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
Multi distance run and walk at Saddle River County Park on December 13, 2026, with timed loops, aid stations, medals, and partial proceeds to an animal rescue.
March 2027
Trail events at Sunken Meadow State Park on a roughly 1.4 mile loop with one hour and three hour formats awarding titles for greatest distance covered.
A 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 2.3 mile loop, on-course food and hydration, a 50 person field, and podium awards for top men and women.
A trail 5K at Bethpage State Park with a free kiddie run, virtual option, post-race refreshments, and age-group recognition.
April 2027
A trail 5K with a free kiddie run at Bethpage State Park, refreshments and a virtual entry option; proceeds support the Never Stop Running Foundation.
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.
A 5K trail run and walk at Blydenburgh County Park with a mixed-surface course, dog-friendly rules, on-site amenities, and proceeds supporting Last Chance Animal Rescue.
A community 5K running event in Woodhaven, NY on April 10, 2027 supporting Jamaica College and its Penn Relays Team; registration fee $20.
A scenic all-terrain 5K and a 0.3 mile kids fun run at Stamford Museum and Nature Center on April 11, 2027, with farm views and a free kids educational dropoff.
Point-to-point 50K and 25K across the Suffolk County Greenbelt Trail from Sunken Meadow to Heckscher State Park, featuring five aid stations and shuttle service.