Trail Running calendar near West Rock 2025-2026

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.

Hit the Brooksvale Trails Turkey Trot at Brooksvale Park in Hamden for scenic 5K and 10K trail runs that are friendly to runners and walkers. Enjoy swag and maple bacon donuts while supporting park trails and a local food drive.

Join a scenic trail 5K or bring kids to a fun run at Hilltop Hanover Farm, a historic working farm and environmental center. This family fun fundraiser gives 5K finishers a $5 farm stand credit and supports the Friends of Hilltop.

Tackle a rolling 8K through the West Hartford Reservoir at the Hartford Track Club 8K Cross Country Challenge on Nov 23, 2025. Enjoy trails, gravel and scenic views as runners vie for age group honors in a fast, fun fall race.

Run a scenic trail half marathon around two glacial lakes and along the Shawangunk Ridge at Minnewaska State Park, with sweeping views into five states. Limited to 300 runners, chip timed with a finisher gift and refreshments.

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.

Join Somers' 7th Annual Thanksgiving Turkey Trot for a scenic but challenging 5K on the cross country trail and a family friendly 1 Mile fun run. Medals for all and shirts for early registrants add holiday cheer.

Run or walk this Thanksgiving on a scenic 5k trail around Scoville Reservoir in Wolcott with medals, swag and timed results. Enjoy pre race stretching and free post race yoga, family and dog friendly, with proceeds supporting EndoFound.

Join the Inwood Hill Turkey Trot, a festive Thanksgiving 5k through scenic Inwood Hill Park in northern Manhattan. Enjoy a family friendly run while supporting the Inwood Food Pantry and celebrating community spirit.

Join the Darien Depot Overstuffed Turkey Trot at Darien High School on Nov 28 for 5K, 1 mile and kids races on scenic cross country trails, with medals for all finishers. Proceeds support The Depot youth center and post race music and food.

Squatchy Leftovers is a scenic trail festival on November 29, 2025 at South Mountain Reservation in West Orange NJ, with distances from a 50K to a kids mile on a rugged 5K loop. Expect technical singletrack, handcrafted wood medals and a ch..

Join the Leftover Turkey Trot, a lively trail 5K at Bethpage State Park with in person and virtual options plus a free kiddie dash. Proceeds benefit the Never Stop Running Foundation and support youth and special needs programs.

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.

Run or walk the Never Stop Running Foundation Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30, 2025, supporting a great cause. Enjoy post race refreshments and a 50 50 raffle with proceeds benefiting the foundation.

Run or walk the Sunday after Thanksgiving at Chesterfield Gorge with a scenic trail 5k, family walk and kids race along the Westfield River. Finishers earn a baked cookie medal and can enjoy a potluck, with proceeds to Hilltown Land Trust.

Run the Tower Tag Challenge at Sleeping Giant State Park on Dec 6, 2025 with 4 and 8 hour timed laps up to the Observation Tower. Scenic carriage roads, aid station support, finisher medal, and proceeds benefit the park association.

The Santa's Summit 10k is a scenic and challenging trail run held at Bull Run Marina in Clifton, Virginia. The course follows the Bull Run Occoquan Trail, featuring hilly terrain with a mix of out-and-back and one-way sections. Participants..

Run a timed 50 miles or 50 kilometers in Prospect Park on a scenic looped course near Lincoln Road. Community aid with Skratch Labs hydration and a potluck style aid station keeps you fueled across the day.