Trail Running calendar near Sterling 2026-2027

Experience New Hampshire’s original 30 hour ultramarathon on the historic Granite Town Rail Trail. Choose from multiple distances and relay options in this flat and fast Halloween themed fundraiser for local trail conservation.

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.

An off road 50k through interconnected woodland preserves in southern Connecticut, featuring rolling forest roads and rocky single track. The event is nonprofit and proceeds support local land conservation, with volunteer roles for aid stat..

Join a community trail race through the diverse terrain of Wompatuck State Park. Choose between a ten mile loop or a 50K distance on a course featuring rail trails and single track paths.

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.

Fall trail races on rugged single-track at Mt. Tom State Park include a 25k, 2-person 25k relay, 10k and a 5k fun run with significant climbing and proceeds benefiting Kestrel Land Trust.

Rugged 5k trail run, ruck, or walk in Berkley MA on October 25, 2026 with in person and virtual options. Dogs may join on leash with a waiver and proceeds support The Baystate Beagle Club and Give2Those.org.

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..

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.

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.

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.

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.

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.

TARC Winter Classic in Stoneham offers 8, 32 and 40 mile trail races on the white blazed Skyline Trail with rugged roots, rocks, frequent climbs and Boston skyline views. Expect technical trails, minimal markings and a festive finish.

Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.

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.