Trail Running calendar near Richmond Hill 2025-2026

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Event overview The Enchanted Forest Ultra Run is a trail ultramarathon held at Roosevelt Forest, 700 Peters Lane, Stratford, CT. The event is offered as a 6-hour format and as a 50K distance. Field size is limited to 50 participants. Regist..

Take on the Terror of Tammany on March 22, 2026 in Worthington State Forest, Columbia NJ. Choose a challenging 30K or epic 50K+ over rugged 6.7 mile loops with big climbs, supportive finish awards, and a true mountain trail test.

The Morris County Empanada Trail Run, held in Morris Plains, NJ, offers both 5K and 10K run/walk events on scenic trails within Central Park of Morris County. The course features mixed terrain including dirt, grass, gravel, and some hills,..

Run the iconic ridgeline at Sleeping Giant State Park on March 29, 2026 with 25K and 50K options that loop scenic singletrack, technical sections and a steep rock scramble up to the Observation Tower. Aid stations will be staffed but this c..

Big Bear Squatch North at Harriman State Park offers a rugged half marathon or 10K over technical trails with steep climbs and scrambling on April 4, 2026. Proceeds support the New York New Jersey Trail Conference and trail care.

Event overview The Long Run is a loop trail event at Jacobsburg State Park in Wind Gap, PA. The course is a give-or-take 5 mile loop that uses single track and flat, fast gravel trails. The loop includes about 450 feet of elevation change a..

Experience Wissahickon Valley Park on scenic, technical single track trails with half and full marathon options. Tackle rolling hills and roots then celebrate at the finish with live music and pizza.

The Spring SOMO Timed Trail Races take place at South Mountain Reservation in South Orange, New Jersey. This event features a looped trail course of 1.88 miles (just over 3K) that includes single track, pavement, and fire road sections. Run..

John Jay Community Trail Race is a community running event in Cross River, New York, on the John Jay Community Cross Country Trail. The event features a 5k Trail Race, a 4k Jay Walk, and a Kids Jay Dash, a 200-meter race. The 5k winds throu..

The Matzah Miles 5k Trail Run and 1 Mile Family Walk is a festive event celebrating Passover, set to take place in Medford, NJ. Participants can choose between a competitive 5K trail run, a leisurely 1-mile family walk, or a fun 50-yard Kid..

Shore2Shore : Apr 18, 2026 Shore2Shore in East Islip, NY is a point-to-point trail race offering the following distances: 50K 25K The race uses the Suffolk County Long Island Greenbelt Trail. The 50K course runs from Sunken Meadow on the..

Squatchywaska Mountainfest is a mountain trail race in Ellenville, NY, offering two courses: 25K and 10 miles. Runners traverse rugged singletrack, cliffs, and crushed-gravel carriage roads on the Shawangunk Ridge, with about 2,500+ ft of e..

Scenic single track, rhododendron tunnels and marsh bridges on a 26 plus mile loop at Wawayanda State Park with distances from Half Marathon to 100K. Camping, aid stations and a crew friendly BaseCamp make it a true trail festival.

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high de..

Join the 52nd Jack Bristol Lake Waramaug Ultra Races in Kent CT on April 26, 2026 for 50K, 50 mile or 100K loops around scenic Lake Waramaug. Expect friendly aid stations, post race food and classic New England views.

XTERRA New Jersey is an off-road multisport event held at the scenic Wawayanda State Park, featuring over 40 miles of trails and a clear lake. Part of the XTERRA World Tour, it offers a variety of races including trail runs (5K to 42K), gra..

The VCP50k is an ultramarathon held in Bronx, New York, founded in 2023 and designed to accommodate both novice and experienced runners. The race features a challenging yet accessible course consisting of ten loops on the classic Tortoise a..

Event overview The Blue 2 Blue Challenge is a 50K trail event in New Haven, CT on May 3, 2026. It is held as an out-and-back that starts at West Rock Playground and follows the blue-blazed trail system. Organizers report a slightly over 80%..

The Green Traill 5K is an annual running event held in Easton, Pennsylvania, specifically at the historic Easton Cemetery. Celebrating its 5th anniversary in 2026, the event features a 5K run, a walk, and a kids fun run for children aged 10..