Darien
Trail Running Calendar near Darien 2026-2027
Explore the top trail runs near Darien 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
A community 5K and untimed fun run at Sachem North High School on November 7, 2026, offering awards, free finish photos, and guaranteed shirts for early 5K registrants.
Trail events at Ward Pound Ridge Reservation: a 10k trail race on November 8, 2026 and a month long Raven 100k Challenge with wooden finisher medallions.
A community 5K at Belmont Lake State Park on November 8, 2026 offering an in-person 5K, virtual option, and a free kiddie dash with post-race refreshments.
An 8K USATF cross-country championship for Open, Masters and Para Athletic divisions at Bethpage State Park on November 8, 2026, for athletes aged 18 and older.
Trail 5K at Bethpage State Park on November 14, 2026 with in person and virtual options, a free Kiddie Dash, family amenities and postrace refreshments.
Backyard Ultra at Cranbury Park in Norwalk, CT where runners repeat a precise 4.167 mile loop every hour until only one runner remains.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Scored 5K cross country at Van Cortlandt Park in the Bronx on November 15, 2026, with youth races, live tracking, and on-site awards.
Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.
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 through Inwood Hill Park on November 26, 2026 with online registration, race-day and advance bib pickup, and proceeds benefiting the Inwood Food Pantry.
Thanksgiving Day 5K and family 1/2 mile fun run at John J Burns Park in Massapequa with certified course, awards, post race snacks, and charity proceeds.
A Thanksgiving Day 5K run and walk at Alley Pond Park with a virtual option, a free kiddie dash, and donations benefiting the Never Stop Running Foundation.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.
A community 5K trail run at Bethpage State Park on November 28, 2026, with in person and virtual options, a free kiddie fun run, bib mailing, shirts, and postrace refreshments.
Trail 5K at Belmont Lake State Park on November 29, 2026 with a cash raffle where 50% of net proceeds are awarded to present participants.
December 2026
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.
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.