Trail Running calendar near Wolcott 2025-2026

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.

Tackle an accurately measured 8K cross country course through the MDC Reservoir Complex in West Hartford on Sunday, November 23, 2025. Rolling gravel and trail terrain with a touch of pavement make this a scenic challenge for all paces.

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.

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.

Run a scenic 5K at Bethpage State Park with the Never Stop Running Foundation Leftover Turkey Trot, offering in person and virtual options. Free kiddie dash with ribbons and proceeds support the foundation.

Join the Never Stop Running Foundation 50/50 Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30. Half of net proceeds are raffled to participants with winners present and the rest supports the foundation.

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.

Celebrate the Sunday after Thanksgiving at Gorge après Gorge in Chesterfield Gorge with a timed 5k, family fun walk, and new kids race. Finishers earn locally baked cookie medals and a warm postrace potluck to benefit Hilltown Land Trust.

Join the Tower Tag Challenge at Sleeping Giant State Park for a scenic timed loop to the Observation Tower, with 4 hour and 8 hour options. Run repeated 3.3 mile laps on a smooth carriage road with aid station support and finisher medals.

Tough Cookie 8K at Sunken Meadow State Park offers scenic cliffside views of the Long Island Sound, festive cookie stops and a post race cookie fest. All paces welcome and proceeds support local charities.

Take on SRC Presents: A Backyard Ultra on Dec 13 to 14, 2025 at Blydenburgh Park, where runners do 4.167 mile laps each hour until one remains. A 1 Lapper runs alongside and proceeds benefit the Long Island Greenbelt Trail Conference.

Run the Frosty Forest 5K in Stratford through Roosevelt Forest on an off road trail welcoming runners, joggers and walkers. Holiday costumes encouraged, every finisher gets a commemorative item and proceeds support local charities.

Join the 8th Annual Taco Trials in Rocky Hill: eat a taco then run a 1 mile loop, repeating it ten times for a fun, quirky challenge. Medals for finishers and proceeds benefit the Connecticut Forest and Park Association.

Seth's Fat Ass 50K at Forest Park in Springfield is a friendly challenge of up to ten 5K loops. You have seven hours to run as many laps as you like, grab event schwag and a t shirt, and enjoy the social ultrarunning vibe.