Trail Running calendar near Kingston 2025-2026

Run or walk a 1 mile, 5k or 10k around scenic Lake Accotink Park to support Reading is Fundamental of Northern Virginia; proceeds help buy books for Title I children. Enjoy medals, tech shirts and a virtual option for all.

Run a scenic 5K at historic Ives Farm in Cheshire, CT, with start and finish at the restored barn. Enjoy family friendly fun from a free Pumpkin Dash for kids to music and crafts while supporting the YMCA and Cheshire Land Trust.

Run or walk the Tough Cookie Trail Run 5K at Prospect Point Park, Lake Hopatcong, on October 25, 2025. Enjoy a scenic 3.1 mile trail while supporting the Jefferson High School football team in this friendly community event.

Join the 9th annual Fall Back into the Trails at Red Wing Recreation Area in Lagrangeville NY for two days of scenic, supported loop trail racing with 10K 50K and 100K options. Custom finisher medals, camping and UTMB index for longer races..

Run or stroll through historic Alice Newton Street Park at the Woodbridge Trail Run plus Woodland Walk, with a challenging two loop 4 mile course and an easy 2 mile walk to the falls. Participants receive custom tech T shirts and post event..

8 Hours at the Farm brings trail runners to Brookfield CT for timed loops on scenic farm and single track trails. Choose 8 hour or 4 hour timed events or a 4 mile race, bring your own cup and race for a handcrafted finisher medal.

Choose Marathon or Half Marathon on a single loop through Rockefeller Preserve, a rolling hilly course with Hudson River and Palisades views amid fields, forests and stone walls. Proceeds support local conservation groups.

Join the 45th Annual Veterans Cross Country 4K at the Northport VA Golf Course on Nov 8 to run a scenic grass course and support hospitalized and homeless veterans on Long Island. Post race snacks, awards, and fun runs add family appeal.

Event overview The Beacon Bonfire 10K is a trail race held on Saturday, November 8, 2025, in Beacon, NY, in the Hudson Highlands. The event is organized as part of the Beacon Bonfire Music + Arts Festival. The race distance is 10K. Course,..

Take on the Raven Rocks 10k trail race at Ward Pound Ridge, starting in the meadow and climbing to Raven Rocks Overlook and the Fire Tower Summit. Enjoy rugged woods, a rewarding downhill finish, and support for Friends of Trailside Museum.

Taconic Road Runners FDR Park Cross Country Run is a cross-country race held in Yorktown Heights, New York, at FDR Park. The event features a 6K course that includes almost two miles of the park’s trail system, with most of the route on sof..

Red, White and Run 5K is a 5K trail run and walk held in Lackawaxen, Pennsylvania, at Veteran's Memorial Park (109 Scenic Drive, Lackawaxen, PA 18435). The course is a trail route designed for both runners and walkers. Special features incl..

Hit the trails at the Red, White and Run 5K in Lackawaxen's Veteran's Memorial Park on November 15, 2025. Enjoy a scenic trail run or walk, friendly competition, and awards for top finishers across age groups.

Test your trail legs at Tarrywile Park in Danbury CT with technical single track, big climbs, and looped courses for 10K, half, and marathon. Rugged scenery, lively finish, and a standout finisher medal.

Event details Fall Fling 400 is organized by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut on November 22, 2025. The event offers two main entry options: 400-minute run on a roughly two-mile loop 4 Mile (two laps of th..

Brooksvale Trails Turkey Trot : November 23, 2025 The Brooksvale Trails Turkey Trot takes place in Hamden, CT, at Brooksvale Park (524 Brooksvale Avenue). The event is organized by Live Loud Running and the Town of Hamden and is the third a..

Join the Roxbury Thanksgiving Day Charity Race for a festive 5K through Everett B. Hurlburt Community Park. Support local causes and burn off holiday calories with friends and neighbors this Thanksgiving morning.

Event details The Squatchy Leftovers is a trail race on Saturday, November 29, 2025, at South Mountain Reservation, 374 Walker Road, West Orange, NJ. Distances offered include: 50K - 10 loops 25K - 5 loops 10K - 2 loops 5K - 1 loop 1 Mile..

Take on a crisp late November trail at Stillwell Woods Preserve in Woodbury on November 30, 2025. Rob's Trail Run Edition features a scenic 5K with separate adult and high school youth divisions for runners of all levels.

Join the Gorge après Gorge for a scenic 5 km trail run or Family Fun Walk at Chesterfield Gorge the Sunday after Thanksgiving. Enjoy handmade hats and cookie medals, a community potluck with hot drinks, and support Hilltown Land Trust.