Trail Running calendar near Pittsfield 2025-2026

Join the 8th Annual Taco Trials in Rocky Hill CT: eat a taco then run a one mile loop, repeat ten times for fun and trophies. All proceeds benefit the Connecticut Forest and Park Association and the event is full with a waitlist.

Seth’s Fat Ass 50K at Forest Park in Springfield on December 20 invites runners to tackle between one 5K loop and the full ten loop 50K in a festive, low key winter setting. Enjoy scenic roads and trails, event swag and a seven hour limit.

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

Join a friendly, informal 5 to 10k run or snowshoe on a roughly 10k course with loaner snowshoes available. Bring a spare pair to share, enjoy light refreshments, and team up for bragging rights and a shared baked treat.

Test your trail skills on the Northern Nipmuck Trail Race, a rugged 16 mile out and back through Yale Myers Forest and Boston Hollow with technical terrain and serious climbing. Limited to 100 entrants, proceeds support local trails.

Tackle rugged singletrack and steep rock scrambles at the Sleeping Giant Trail Runs in Hamden CT on March 29, 2026. Choose a challenging 25K loop or a double 50K and enjoy aid stations, medals and post race food and drinks.

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.

Take on rugged Traprock at Penwood State Park in Bloomfield CT on April 18, 2026 with 17K one loop or 50K three loop options. Expect rolling, technical single track and rocky trails; bring your own cup for this cupless, chip timed race.

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.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 serves up technical singletrack on the Shawangunk Ridge with 25K and 10 mile options, big climbs and sweeping Catskill views. This rugged trail event also supports protection of..

Run the 52nd Jack Bristol Lake Waramaug Ultra Races on April 26, 2026 in Kent CT with 100K, 50 mile and 50K options around scenic Lake Waramaug. Flat rolling loops, four aid stations and finisher swag make this a rewarding spring ultra.

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..

Join A Run to Remember on May 2 in Red Hook and run or walk scenic farm trails through meadows, orchards, and woods at Greig Farm. Honor loved ones, celebrate community spirit, and vie for cash prizes in the 5K and 10K races.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Blue 2 Blue Challenge is a rugged 50K through New Haven trails, with about 6350 ft of climbing and technical rocky terrain including a summit at Mt Sanford. Expect a cutoff driven, no frills race for seasoned trail runners.

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

TARC Wapack and Back is a rugged trail race along the Wapack Trail in Ashburnham offering 21.5, 43 and 50 mile options. Expect technical rocky singletrack, big climbs and limited entries so register early for a backcountry challenge.

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.

Enjoy a scenic 5k at Ledge Rock Hill Winery in Lake George with a cross country style course and options to volunteer and run. Finishers get a medal that doubles as a wine stopper, a shirt and a wine pour.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..