Trail Running calendar near Pittsfield 2025-2026

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.

Get festive at the Ugly Sweater 5K in Canajoharie on December 6, 2025, where runners and walkers hit the scenic Erie Canal trail in holiday style. All proceeds support the Community Youth Center and age group prizes add extra fun for racers..

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 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..

Celebrate spring at the Brooklyn Cider House Spiked Apple 5K on April 19 in New Paltz, a scenic two lap run through vineyards and orchards. Enjoy a cider pour, fresh donut, finisher medal and commemorative shirt.

Tackle rugged singletrack, cliffs and glacial ledges on the Shawangunk Ridge in this scenic mountain trail race offering 25K and 10 mile courses. Proceeds support Run Wild's campaign to protect Verkeerder Kill Falls.

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..

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

On May 3 2026 Breakneck Point Trail Runs in Beacon NY offers a half at about 14.5 miles and a full at about 26.5 miles on rugged, technical trails with steep climbs and exposed sections. Expect big elevation, scenic views, aid stations, and..

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.

Run the scenic Dandelion Dash 5K on The Hartsbrook School trails or enjoy the family friendly Mushroom Mile in Hadley, MA. Support school programs in sustainable agriculture and beekeeping or run virtually from anywhere.

Run the rugged Wapack Trail in Ashburnham MA with 21.5, 43, or 50 mile options on May 9, 2026. Limited entries for this technical, scenic trail run benefit land conservation through the Trail Animals Running Club.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.