Trail Running calendar near Smithtown 2026-2027

Honoring September 11 heroes, this arena climb at TD Bank Ballpark features a 2,200 foot track through stadium aisles. Join a timed stair challenge or a flat concourse walk to support the Tunnel to Towers Foundation.

A 7-mile USATF sanctioned trail race in Barkhamsted, CT on 08/01/2026. Registration runs 05/03/2026 to 07/31/2026 with a $20 fee and no race day registration; results posted online by Greystone Electronics.

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.

A scenic 2.5 mile trail run and walk at Wildwood State Park on August 8, 2026, with live results, free finish line photos, and personalized bibs for early registrants. Proceeds benefit the Friends of Wildwood State Park.

Tappen Brook 5K on August 9, 2026 in Bridgewater, CT is a 3rd annual trail race on the new Bridgewater Town Park trails, featuring packed-dirt paths, gentle hills and views of Lake Lillinonah. The event is organized by local land trust and..

Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.

An evening 3.6 mile trail run through Forest Park in Queens that visits 543 acres of wooded trails with rolling hills. After the run a festival area has music, vendors, food trucks and awards with participant tees provided.

Trail races at Fahnestock State Park near Cold Spring, NY on Aug 15, 2026. Distances include 50K, 25K, and a 5.5-mile option on mixed dirt roads and technical single track with on-course aid and a post-race meal.

Experience a community trail run through Elm Ridge Park benefiting the Rocky Hill Fire Department and Library. This event features a two loop trail course for adults and a fun medal race for kids.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

A 50K in Forest Park, Queens, run on a 2.5 mile loop repeated 12 times with about 300 feet of elevation per loop. Aid stations are provided after each lap and there is an eight hour cutoff for the race.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

Barn B Q Trail Festival on Saturday 9/5/2026 at Masker's Barn pairs a trail run or hike with a five hour barn party featuring BBQ, drinks, music and games. Ticket options cover adults, designated drivers, and children.

An obstacle-based 5K at Short Beach in Stratford on September 12, 2026, with 18+ obstacles and family-friendly rules. Proceeds benefit the Sterling Community Center and registrations include a race shirt and finisher medal.

City Challenge Race returns to Jersey City on September 12, 2026 with a fast 3-mile urban obstacle course featuring 20+ city-style obstacles, new finisher medals, professional chip timing, awards and free race photos.

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

A timed trail festival in Pawling, New York offering 24 hour, 12 hour day and night, 6 hour and 3 hour races on a short mixed surface loop with aid stations, crew areas, finisher medals, and distance based awards.

A multi-day trail festival in Ringwood New Jersey, mid-September 2026, offering races from a one mile kids event to a 100 mile race with a 36 hour cutoff, free camping, community programming, and nonprofit partnerships.