Trail Running calendar near Middlefield 2026-2027

Run or walk through the scenic trails of Blydenburgh Park this autumn. Participants enjoy a 5K trail course complete with seasonal treats and commemorative event swag.

Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.

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.

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..

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.

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.

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.

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..

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

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.

USATF Long Island hosts Open, Masters and Para Athletic cross country championships over an 8K course on November 8, 2026. Online registration is closed.

Experience a seasonal 5K trail run or walk through the scenic paths of Bethpage State Park. This family event features local refreshments and a welcoming atmosphere for participants of all abilities.

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.

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.

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.

Celebrate the holiday at the Inwood Hill Turkey Trot 5K Run and Walk. This event offers a scenic course through Inwood Hill for participants of all abilities to enjoy a morning of fitness and community.