Massapequa
Trail Running Calendar near Massapequa 2026-2027
Explore the top trail runs near Massapequa for 2026-2027! We've gathered 35 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A family friendly 5K trail run or walk at Bethpage State Park on November 14, 2026 with a free kiddie dash, post race refreshments, finisher photos and a virtual option.
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 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.
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
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.
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 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 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.