Massapequa Park
Trail Running Calendar near Massapequa Park 2026-2027
Explore the top trail runs near Massapequa Park for 2026-2027! We've gathered 34 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A stair-climb race at the Empire State Building ascending 86 flights (1,576 steps) with multiple entry categories and specified registration windows.
Trail half marathon in New Rochelle running a single loop through five Westchester parks on mostly dirt shaded trails with frequent wildlife on October 11, 2026.
A scenic trail 5K at Blydenburgh County Park on October 11, 2026 with in-person and virtual options, race tee, refreshments, and age-group recognition.
Multi day running weekend in Bay Shore, NY with marathon, half marathon, 10K, 5K, kids 1K, relay and a virtual 26.2 miles challenge.
A community 5K and kids fun run in Massapequa Park supporting officer mental health and suicide awareness, with medals, awards, and finish-line photos.
November 2026
Community 5K and untimed fun run on November 7, 2026 at Sachem North High School in Lake Ronkonkoma NY, offering shirts, live results, photos, and age group awards.
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 5K run and virtual 5K at Belmont Lake State Park on November 8, 2026 featuring a scenic lakeside course, a free kiddie dash, event swag, and age-group recognition.
Championship cross country at Bethpage State Park on November 8, 2026 featuring an 8K Open, Masters and Para Athletic competition with individual and team awards.
A family-friendly trail 5K at Bethpage State Park on November 14, 2026 with in-person and virtual options, a free Kiddie Dash and post-race refreshments.
A 5K run/walk in Inwood Hill Park on November 26, 2026, benefiting the Inwood Food Pantry with live results and free finish-line photos.
Thanksgiving Day 5K run plus a 1/2 mile fun run at John J Burns Park in Massapequa supporting the John Theissen Children’s Foundation and the Leukemia and Lymphoma Society.
A Thanksgiving 5K at Alley Pond Park with in-person and virtual options, a free kiddie dash, race shirt and post-race refreshments.
A community Thanksgiving run at Darien High School featuring a 5K and 1-mile walk/run, with music, food, and proceeds benefiting The Depot youth center.
A trail 5K at Bethpage State Park on November 28, 2026 offering in-person and virtual options, a free kiddie dash, race shirts and post-race refreshments.
A trail 5K at Belmont Lake State Park on November 29, 2026 with cash prizes from a raffle that awards 50% of net proceeds to present participants.
Nine mile cross country race in Van Cortlandt Park using three loops, with commemorative buffs for early registrants and awards from Lloyd's Carrot Cake.
December 2026
A looped ultramarathon in Prospect Park offering 50K and 50 mile options, one aid station with Skratch hydration, chip timing, a 15 hour cutoff, and finisher buckles.