Trail Running calendar near Great Barrington 2026-2027

Run the Jug End Loop Ultra in the scenic Jug End State Reservation. Choose between a 4.2-mile race or a 6-hour ultramarathon on a challenging loop trail. All finishers receive a handmade ceramic mug, and the event supports local charities.

This 4-mile trail run in Schenectady Central Park uses a flexible time trial format. All proceeds support addiction recovery services, honoring a personal legacy. A pre race stretching session is included.

Experience a scenic trail festival at Thacher State Park featuring races from 10k to 50k miles. Run through wide paths and single track trails with beautiful escarpment views in a sustainable cupless event.

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.

Explore the scenic Shawangunk Ridge on a rugged 70-mile trail. Choose from three distances: a 70-miler, 30-miler, or half marathon. This unsupported event celebrates the preserved beauty of the 'Gunks' mountains.

Explore the singletrack of Macedonia Brook State Park in Connecticut. Choose from 12K, 25K, or 50K distances on a course featuring climbs, technical trails, and the famous viewpoint atop Cobble Mountain. Enjoy a post-race celebration with f..

The Where the Pavement Ends trail race offers a technical 4.25-mile single loop or an 8-mile double loop through the Hemlock Hills. It's part of the multi-race Trail Mix Series. Both races start and finish at the Lake Windwing ballfields in..

Run a scenic 5K trail race through 300 acres of natural terrain at Winding Trails in Farmington. Compete for age group awards and the local Lee Chisholm Award on a course surrounding Walton Pond.

A point-to-point, rugged trail marathon with nearly 7000 feet of elevation gain in New York's Catskill Mountains. The route features technical climbs, scenic views, and multiple aid stations, with proceeds supporting land conservation.

Experience a scenic trail run through wooded hillsides and fields near the Wallkill River. Choose between a 5k or 10k race on single track trails and participate in the local athletic sneaker recycling program.

Experience a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

This 24-hour trail challenge in Cornwall, CT, covers over 28 miles and 13,685 feet of elevation gain. Participants can run, hike, or walk the double marathon distance or tackle it as a relay.

The NipMuck Trail Marathon is a classic 26.4-mile race on Connecticut's rugged Nipmuck Trail. Runners can also team up for a two-person relay. The event supports local trail programs through the nonprofit Shenipsit Striders running club.

Experience the seasonal scenery of New Hampshire at the Keene Family YMCA Fall Foliage Trail Race. Choose between a fast 5K or a 10K with elevation gain to support local community programs.

Challenge your legs on the slopes of Mohawk Mountain Ski Resort in Cornwall, CT. Choose from marathon, half marathon, 10K, or 5K distances on a course featuring climbs, descents, and fall foliage views. Hikers are welcome on the shorter tra..

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

This 3.5-mile trail run/walk on the flat Mill Pond Trail happens in Wolcott, CT. The Wolcott Lions Club hosts the event, which includes a race t-shirt and clam chowder. Registration opens online with a lower early-bird rate.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

Experience peak autumn foliage at the Mt. Tom Trail Race featuring a 25k solo or relay, a 10k, and a 5k fun run through rugged Massachusetts state park trails with significant elevation.

Experience a unique trail race through the forests and meadows of Muscoot Farm. Enjoy distances for all ages followed by a visit to the local farmers market with your farm buck vouchers.