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
Community 5K and untimed fun run on November 7, 2026 at Sachem North High School with T-shirts, live results, finish line photos, and age group awards.
A 46th annual 4K cross country at the VA Golf Course in Northport with proceeds supporting hospitalized and homeless veterans; includes a free short fun run and a virtual 4K.
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.
A community 5K at Belmont Lake State Park on November 8, 2026 with in-person and virtual options, a free kiddie dash, and proceeds supporting the Never Stop Running Foundation.
Cross country championship 8K at Bethpage State Park on November 8, 2026, for Open, Masters and Para Athletic divisions with age-group and team awards.
A scenic second-annual 5K at the New York Botanical Garden on November 8, 2026, combining road and trail sections with post-run festivities and garden views.
Family friendly 5K trail run and walk at Bethpage State Park on November 14, 2026, with a virtual option, a free kiddie dash, and post race refreshments.
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.
Thanksgiving Day 5K and family fun run at John J Burns Park in Massapequa with a USATF certified 5K course and proceeds benefiting two charities.
A community 5K and free Kiddie Dash at Alley Pond Park with in-person and virtual options 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.