Trail Running calendar near Holyoke 2026-2027

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

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.

Run through history on New Hampshire's Granite Town Rail Trail. This October event offers races from a 15-mile run to a 30-hour ultramarathon, all benefiting local trail conservation. The fall foliage creates a memorable backdrop for this u..

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.

Experience the diverse landscapes of Westerly and Hopkinton in this trail race series event. Runners can choose between 10K and 10 mile distances featuring riverfront views and technical single track paths.

Run a scenic autumn 5k trail through Wrentham conservation land and a working farm. This cup-less race supports local agriculture and includes family Halloween fun. It's the final event of the Farm to Trail 5K Series.

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.

Tackle a unique mountain course that goes up and down four times over 4.9 miles. The event offers prize money, age group awards, and benefits the Keene Community Kitchen. Early registration includes a t-shirt.

This fall trail run takes place at Powisset Farm in Dover, MA, featuring four scenic distances through farm and woodland trails. Post-race cider donuts and family activities like pumpkin painting add to the farm atmosphere. It's part of the..

The Fall Back Into The Trails Series returns to New York's Red Wing Recreation Area. Runners can tackle a 100k, 50k, or 10k on challenging, looped courses. All finishers earn a custom medal, and the ultras are UTMB Index races.

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

Experience an obstacle course race inside the historic Fenway Park stadium. This event features a 5K course with 20 obstacles and dedicated races for children through the iconic home of the Boston Red Sox.

Test your endurance at this backyard ultra in Winchendon featuring a 4.1666 mile loop through fields and trails. Choose from the last runner standing format, timed races, or a single lap challenge in a relaxed community setting.

TARCkey Trot is a 6 hour trail challenge at Wright Locke Farm of repeated 5K loops with rocky rollers. Run as many loops as you wish and bring your own hydration for this cupless event.

Experience technical Northeast single track trails and 3000 feet of elevation at Tarrywile Park. Choose from 10K, Half Marathon, or Marathon distances featuring scenic lake views and a sustainable cupless environment.

A trail race at Burlingame State Park in Charlestown on November 15, 2026, offering 4-mile and 8-mile courses around Watchaug Pond. It is the first race in the WTAC fall trail series with multi-race registration discounts.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

Test your endurance at YMCA Camp Sloper with a 400 minute timed challenge or a 4 mile trail race. Explore rolling wooded trails in Southington while supporting local charities and youth running programs.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.