Trail Running calendar near Smithtown 2026-2027

A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.

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.

Trail races at South Mountain Reservation include 5K, 10K and 13.1 mile looped courses with aid stations every 3 miles. Courses use fire roads, single track, hills and some pavement and offer advance and day-of registration.

A January trail party using a 5K loop with three hour and six hour options plus a 3H ruck. Mixed carriage roads and technical singletrack, limited field size, and proceeds benefit the South Mountain Conservancy.

A winter trail event at Ramapo Valley County Reservation on February 14, 2027 featuring a flat, scenic lollipop loop around Scarlet Oak Pond. Participants are encouraged to wear onesies; the event includes an aid station, finishers medal, a..

Trail races on a 10 mile loop at South Mountain Reservation offering 50M, 50K, 20M and 10M with marked trails, three aid stations per loop, timing, SWAG, and awards for top three male and female finishers.

A lap based time race on a USATF certified flat course in Livingston, NJ offering 12 hour, 6 hour, 3 hour and 1 hour races. Awards and participant hats are provided and aid stations are available on course.

A looped trail event on March 6, 2027 at South Mountain Reservation in West Orange, NJ offering 11 mile, 20 mile, 50K and 50 mile options on three marked loops with mixed carriage roads and technical singletrack.

Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and f..

A six hour trail ultra at Roosevelt Forest in Stratford, CT on March 20, 2027, offering a 50K option on a 2.3 mile loop of roots, rocks and rolling hills, with a capped field of 50 entrants and on-course food and hydration.

A 5K trail run at Bethpage State Park with a free kiddie fun run and a virtual option, a good luck shirt, on course hydration, post race refreshments, and age group recognition. Beer is available for participants 21 and older with ID.

A 5K trail run and a free kiddie run at Bethpage State Park with in-person and virtual options, onsite refreshments, mailed bibs, and online results. Donations support the Never Stop Running Foundation.

A mountain trail event at Harriman State Park offering a half marathon, a 10K, and a 10K ruck on rugged, technical courses with significant elevation gain and limited crew access at aid stations.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY, on mixed terrain with dog friendly policies. Event proceeds support Last Chance Animal Rescue and online recognition is given for top age group finishers.

Trail races at Penwood State Park on April 17, 2027 include a three-loop 50K and a single-loop 17K over rocky, rolling single track and double-track. The event is cupless, has a waitlist, and is organized by the CT Trailmixers.

A weekend obstacle course at Mountain Creek Resort in Vernon NJ on April 24–25, 2027, offering Sprint 5K, Super 10K, Beast 21K, Ultra 50K and kids races, plus a Trifecta Weekend option and team entries.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.

XTERRA New Jersey on April 24 and 25, 2027 brings trail runs, triathlon, duathlon, paddle tri and mountain bike races to Stokes State Forest, with World Tour and Trail Run World Series events and World Championship qualification slots.