Trail Running calendar near Westfield 2026-2027

Trail races at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k and 10k looped courses with significant elevation. The 50k and 100k hold UTMB Index status and provide aid stations plus finisher medals.

This 8-hour timed trail run takes place on the rolling farm trails at Gurski Farm in Brookfield, CT. Runners complete as many laps as possible on a course featuring single track. It offers a community atmosphere where participants frequentl..

A backyard ultra at Kenty's Farm on a 4.1666 mile loop where runners repeat hourly laps until one remains. Timed options of 6, 12 and 24 hours and single-lap entries are also available.

A trail 10k at Ward Pound Ridge Reservation plus a November virtual 100k challenge, with race results, photos, and a custom finisher woodallion for 100k finishers.

Trail race at Tarrywile Park in Danbury, CT, offering Marathon, Half Marathon and 10K on technical, hilly single-track trails with finisher medals, podium awards and a $600 half-marathon time bonus.

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.

A trail half marathon in Roosevelt Forest using eight 1.64 mile loops to total 13.1 miles. The event includes pavilion aid each loop, a book drive with Books4Everyone, costume prizes, podium awards, and participant swag.

Trail races at YMCA Camp Sloper in Southington CT feature a timed 400 minute loop event and a 4 mile two lap race on a roughly two mile wooded course. The event includes an aid station, chip timing, and finisher medals.

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.

An annual Roxbury Road Runners charity race held on Thanksgiving Day, with proceeds supporting the Roxbury Scholarship Foundation and the Roxbury Ambulance Association. Results for the race are published as part of the club series.

A trail running event at Sleeping Giant State Park on December 5, 2026, using the park's varied trails and scenic viewpoints. Organized by Steep Endurance with entry fees listed between 50 and 80 USD.

A 5K trail event through Roosevelt Forest in Stratford, CT on Dec 19, 2026, open to runners, joggers and walkers. Holiday costumes are allowed, awards recognize the fastest three men and women, and proceeds benefit local organizations.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

Trail races at Sleeping Giant Park in Hamden, CT offering a 25K loop with 3K+ vertical and a 50K two loop option. The course features technical singletrack, steep rock scrambles, aid stations, and finisher medals.