Trail Running calendar near Litchfield 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.

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 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.

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.

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.

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.

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.

Join the West Rock Winter Fat Ass in Hamden CT on Dec 28, 2025 for eight hour loop fun around Lake Wintergreen. Run repeated 1.6 mile laps with aid and snacks in a 50 runner field while supporting Make a Wish and the American Cancer Society..

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.

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Run under the pines at the Enchanted Forest Ultra Run in Roosevelt Forest, Stratford CT, offering a 6 hour or 50K timed trail challenge on rugged trails. Only 50 entries, costumes welcome, with pizza, aid stations and medals.

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

Take on rugged singletrack, a steep headwall scramble and 3,000 feet of climbing at Sleeping Giant Trail Runs, with 25K and 50K options. At Sleeping Giant State Park in Hamden CT on March 29, proceeds benefit the park and finishers get meda..

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 Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.