Trail Running calendar near Shandaken 2025-2026

Join the 9th annual Fall Back Into The Trails Series at Red Wing Recreation Area in Lagrangeville on Nov 1 and 2, 2025 with options from a single 10k to a rugged 100k across looped trails. Aid, camping and custom finisher medals await.

Challenge yourself in the Saratoga Stryders Fall Back 5 Mile Trail at Saratoga Spa State Park, featuring rolling ridges, single track, grassy stretches and a stair climb. Enjoy a scenic, challenging course and post race prizes.

Challenge yourself at Steep Endurance's 8 Hours at the Farm in Brookfield, a rolling 4 mile loop of single track and farm trails. Choose 8 hour, 4 hour, or 4 mile distances, enjoy finisher swag, and support local nonprofits.

Run the scenic Pocantico Hills Marathon or Half Marathon on Nov 8 2025 in Sleepy Hollow NY, a loop through Rockefeller State Park Preserve with rolling hills and Hudson views. Proceeds support local park and trail groups.

Run a scenic 10K up Mt Beacon to the firetower and back on rugged Hudson Highlands trails with steep climbs and autumn views. Part of the Beacon Bonfire festival, the race ends with refreshments, a shirt and festival perks.

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..

Run the 19th Annual Age Before Beauty 5K cross country at White Memorial in Litchfield, Connecticut on Sunday, November 9, 2025. Enjoy a scenic conservation trail course that welcomes all ages and abilities.

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.

Run scenic, hilly single track at the Tarrywile Half Marathon on November 16, 2025 in Danbury CT with 10K, half marathon and marathon options. Rugged terrain, aid stations and finisher medals make for a rewarding trail day.

Brave frosty singletrack through scenic Ringwood woods with 5K, 10K and half marathon options for every trail runner. Finish with a warm post race party serving food, drinks and winter views.

Join the Roxbury Thanksgiving Charity Race, a scenic 5K in Roxbury, Connecticut, starting and finishing at Everett B. Hurlburt Community Park. Run or walk to celebrate the season and support local causes.

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.

Enjoy winter trail runs and a snowshoe race at Chenango Valley State Park during the Binghamton Pond Festival, with festival vibes near the start. Choose 10k, 20k or 50k loops or a free kids run and support local youth programs.

Dress in your best onesie and tackle scenic trails at Squatchy Onesiefest in Ramapo Valley. Choose a fun 1.6 mile loop or a two lap 5K, enjoy trail support and a handcrafted finisher medal while supporting the NY NJ Trail Conference.

The Bullshit Backyard Ultra in Lenoxville, PA is a Last Person Standing race where runners repeat a loop each hour until one remains. Daytime farm trails and a night field and road loop create a gritty, unforgettable test.

Run rugged trails at Big Bear Squatch North in Harriman State Park on April 4, 2026 with half marathon, 10K and ruck divisions. Expect steep climbs, scrambling terrain and sweeping Hudson Valley and NYC skyline views.

Run the John Jay Community Trail Race in Cross River on Sunday April 12, 2026 for a scenic 5k through wooded, hilly school trails and a family friendly 4k walk. Kids can sprint the 200 m Jay Dash on the track and celebrate a student built c..

Tackle rugged singletrack, cliffs and glacial ledges on the Shawangunk Ridge in this scenic mountain trail race offering 25K and 10 mile courses. Proceeds support Run Wild's campaign to protect Verkeerder Kill Falls.