Trail Running calendar near Goshen 2025-2026

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.

Celebrate Thanksgiving in Springfield VT at Toonerville Trail Turkey Trot, a flat, scenic 5K along the Black River with a virtual option to support local food banks and school teams. Finishers get socks and cider donuts.

Join a scenic road and rail trail run with prizes for top finishers. Route may change for weather and the event will be canceled if it snows. Entry is donation based; proceeds benefit a local dog rescue and community theater.

Celebrate Thanksgiving on the trails at the F.I.T. Turkey Trot Trail Race in Cumberland, Rhode Island on November 27. Choose from 5K, 5 Mile, combo, multilap or a Kids Race and earn a unique finisher medal.

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.

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.

Take on the Tower Tag Challenge at Sleeping Giant State Park on December 6 with 4 hour or 8 hour timed options of repeated out and back laps to the park observation tower. Enjoy the scenic climb, earn a finisher medal, and support the park.

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.

The Gurney Lane 5K Snowshoe Race will take place in Queensbury on Saturday 17 January 2026. You can run 5 kilometers.

The Dar Snowshoe Scramble will take place in Goshen on Sunday 25 January 2026. You can run 10 kilometers.

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.

Tackle the Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT on March 29, 2026 with 25K and 50K options across rugged singletrack and big climbs. Expect steep scrambles, more than 3,000 feet of gain per loop, cupless aid s..

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.

Run a scenic 6.55 mile quarter marathon through West Hartford Reservoir 4 as two loops around the park. Limited to 150 runners, the event features chip timing, post race treats and awards in five year age groups.

Tackle rugged trails at Penwood State Park in Bloomfield CT with the Traprock race, offering a single loop 17K or a three loop 50K on scenic, rocky Metacomet Trail. Hosted by CT Trailmixers, this cupless trail run supports local land trusts..

TARC Spring Classic in Weston MA on April 25, 2026 offers 10K, half, marathon and 50K trail races plus a free youth fun run on a smooth scenic 10K loop. This cupless, multi lap event fills fast so register early as parking and aid are limit..

Run the 52nd Jack Bristol Lake Waramaug Ultra in Kent CT on April 26 2026 for scenic, mostly flat loops around the lake with 100K, 50 Miler and 50K options. Expect stocked aid stations, finisher swag and lakeside views to inspire.

Tackle the scenic Seven Sisters Trail Race in Amherst, MA on May 2, 2026, an out and back along the Holyoke Range ridgecrest. This rugged 12 mile course delivers steep climbs, rocky singletrack and over 3,500 ft of elevation for a thrilling..

Blue 2 Blue Challenge is a demanding 50K on May 3, 2026 in New Haven, Connecticut, across rugged blue blazed trails with steep, technical climbs. Entry is by waitlist and requires a recent qualifying trail 50K, so come prepared.