Massapequa
Trail Running Calendar near Massapequa 2026-2027
Explore the top trail runs near Massapequa for 2026-2027! We've gathered 36 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Outrun the Stigma 5K Run/Walk in Massapequa Park on October 24, 2026 features a 5K and kids fun run with medals, awards, photos and an after party.
A community 5K run/walk in Forest Park, Queens on October 25, 2026, with a free 1K kids run, participant T-shirts, and medals for early registrants and top finishers.
November 2026
A community 72nd anniversary event in Lake Ronkonkoma with a timed 5K run/walk and an untimed fun run on mixed pavement, grass and trail surfaces.
A 4K grass cross country event at the Northport VA Golf Course with military and youth categories, a short fun run, awards, and proceeds supporting local veterans.
A community 5K at Belmont Lake State Park on November 8, 2026 with in person and virtual options, a free kiddie dash, post race refreshments, and proceeds supporting NSRF.
USATF Long Island 8K Open and Masters Para Athletic XC Championships on November 8 2026 at Bethpage State Park Playground in Bethpage NY
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.
A family 5K trail run and virtual option at Bethpage State Park on November 14, 2026 with a free kiddie dash, post-race refreshments, and proceeds supporting the Never Stop Running Foundation.
Six hour timed run and relay at Belmont Lake State Park on November 15, 2026 featuring individual and team entries on a 2.50 mile loop with post event food and awards.
A community 5K through Inwood Hill Park on November 26, 2026 with proceeds benefiting the Inwood Food Pantry and on-site bib pickup options.
Thanksgiving Day 5K and family half mile fun run at John J Burns Park in Massapequa with race shirts, age-group awards, and proceeds benefiting local charities.
A Thanksgiving 5K at Alley Pond Park with a three-loop course, a free kiddie dash, virtual option, race shirts, and donations 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.
A trail 5K run and walk at Bethpage State Park on Nov 28, 2026 with a virtual option, a free kiddie dash, event shirts, and postfinish refreshments.
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 trail 5K at Belmont Lake State Park in late November 2026 featuring a 50/50 raffle where half the net proceeds are awarded to present participants.
December 2026
A looped ultramarathon in Prospect Park offering 50 mile and 50K options, one aid station per lap, a 15 hour cutoff, and finisher belt buckles.
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.