Trail Running calendar near Poughkeepsie 2025-2026

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.

Join the 45th Annual Veterans Cross Country 4K at the VA Medical Center golf course on November 8, 2025. Scenic grass course, a free half kilometer fun walk, awards and snacks with proceeds supporting hospitalized and homeless veterans.

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.

Join Taconic Road Runners for a relaxed 6K through FDR Park on November 9, 2025, now held as a club fun run and meeting. Enjoy soft trails, commemorative running gloves and hot drinks by the warming fire while you meet fellow runners.

USATF Long Island hosts an 8K cross country championship at Bethpage State Park on Nov 9, 2025 for adults 18 and over. Competitive team and individual racing with medals and live results make for a great fall race.

Join a 24 hour vigil run at Kean University honoring those who served while keeping someone on the track for the full day. Proceeds support Mission 22 and its veteran wellness programs.

Join the Dave Driscoll 19th Annual Age Before Beauty 5K cross country at White Memorial in Litchfield on Sunday, November 9, 2025. Enjoy a scenic all cross country course as the first race of the day ahead of the Junior Olympics.

Join the Red, White and Run 5K trail run and walk at Veteran's Memorial Park in Lackawaxen on November 15, 2025. All paces welcome with day of registration and awards for top finishers across age groups.

Run or walk a scenic 5K at Bethpage State Park for the Never Stop Running Foundation Turkey Trail Trot, with a free Kiddie Dash and virtual option. Join November 15, 2025 to support the foundation and enjoy post race treats.

Run Staten Island's scenic singletrack at NYC Trail Mix on Nov 15 2025, weaving through Blood Root Valley, High Rock and La Tourette. Choose 50M, 50K or half marathon distances and support the Greenbelt Conservancy.

Hit the trails at South Mountain Reservation in South Orange on November 15, 2025 for NJ Trail Series SOMO Winter 1. Choose from 5K, 10K or 13.1M looped routes featuring fire roads, single track and rolling hills.

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.

Chase a fast PR at the Last Chance XC Championships in Oak Ridge Park, Clark NJ on November 16. The USATF New Jersey 8k championship runs on a double loop pancake flat course, with personalized bibs, oversized medals and free action photos.

Run the Brookhaven Trail Half Marathon or 5 Mile through single track, fire trails and sandy woodlands at Brookhaven State Park near Wading River NY. Half marathoners vie for cash, a wood finisher medal and post race refreshments.

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.

Join a lively 5K at Clifton City Hall on Sunday, November 16, 2025, featuring a race T shirt and postrace music, raffles and healthy snacks. Age group awards and special recognition for first responders add extra excitement to this 500 poin..

Take on the Fall Fling 400 at YMCA Camp Sloper in Southington CT on Nov 22, 2025. Choose a unique 400 minute loop endurance challenge or a 4 mile two lap trail race through wooded single track and rolling hills.

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 4th Annual Sargent Elementary Turkey Trot in Beacon, NY for a family friendly 5K on the scenic Long Dock Park trails plus a Kids Fun Run on campus. Enjoy a food drive, live DJ, refreshments, awards and new team sign ups.