Trail Running calendar near Leyden 2025-2026

Test your endurance at the Hamsterwheel in New Boston, NH on Nov 1. Choose 6 to 30 hour solo or relay divisions on a scenic, mostly flat 4 mile loop along the rail trail, and earn a special belt buckle for reaching 100 miles.

Moreau Half is a scenic, challenging 14 mile trail race around Moreau Lake State Park on November 1, 2025. Expect technical singletrack, big climbs and a true backcountry feel for a rewarding day on the trails.

The Hugs from Vets Trail will take place in Henniker on Sunday 2 November 2025. You can run 10 kilometers.

Challenge yourself in the Saratoga Stryders Fall Back 5 Mile Trail at Saratoga Spa State Park, featuring rolling ridges, single track, grassy stretches and a stair climb. Enjoy a scenic, challenging course and post race prizes.

Run the 21st annual GFRC Busa Bushwhack on November 2, 2025 in Framingham, tackling scenic, technical trails in Callahan State Park over 5.3 or 10 miles. Finish at Brophy Elementary, grab a cooling towel and compete for log trophy awards.

Push your limits at Race for DFL, a backyard ultra at Kenty's Farm in Winchendon MA where runners repeat 4.1666 mile laps until only one remains. Choose 6, 12 or 24 hour options and enjoy themed laps, fun gear and great camaraderie.

Join the Centerville Bank Thompson Turkey Trot on November 9 for a family friendly cross country 5K, 3K Wobble walk and kids fun run with costumes encouraged. Proceeds benefit Thompson trails, parks and the local food pantry.

Run scenic single track and forest roads at the Upton 10.5K and Half Marathon, a hilly, technical trail challenge in Upton State Forest. Enjoy a small field, post race fire pits, hot soup and chocolate, and support local charities.

Join the Dave Driscoll 19th Annual Age Before Beauty 5K cross country at White Memorial in Litchfield on Sunday, November 9, 2025. Enjoy a scenic all cross country course as the first race of the day ahead of the Junior Olympics.

Join the TARCkey Trot, a six hour timed challenge at Wright Locke Farm on November 15, 2025, running multiple 5K trail loops over rocky rollers. Tackle as many laps as you like while supporting land conservation.

Join Windham Woods School for the 2nd annual Thankful Trails 5K Run and Walk through scenic campus trails, plus a free Kids Fun Run on the Lower Field for ages 8 and under. Family friendly with raffle, awards, and lunch to celebrate communi..

Test your grit at the Mount Ascutney Vertical Backyard, a Last Person Standing uphill race in Brownsville VT where runners repeat hourly laps of steep ascent until only one remains. Aid, indoor facilities and camping are available.

Take on the Fall Fling 400 at YMCA Camp Sloper in Southington CT on Nov 22, 2025. Choose a unique 400 minute loop endurance challenge or a 4 mile two lap trail race through wooded single track and rolling hills.

Join the 27th annual Novemberfest Race, a scenic 4 mile run through Mine Falls Park in Nashua on Sunday, November 23, 2025. Celebrate at Martha's Exchange with raffle prizes and beers while supporting the Nashua Children's Home.

Tackle an accurately measured 8K cross country course through the MDC Reservoir Complex in West Hartford on Sunday, November 23, 2025. Rolling gravel and trail terrain with a touch of pavement make this a scenic challenge for all paces.

Join a scenic road and rail trail run with prizes for top finishers. Route may change for weather and the event will be canceled if it snows. Entry is donation based; proceeds benefit a local dog rescue and community theater.

Join the Toonerville Trail Turkey Trot, a flat 5K along the Black River in Springfield on Thanksgiving, with in person and virtual options. Proceeds and a food drive support local food shelves, and finishers receive a pair of Turkey Trot so..

Run or walk this Thanksgiving on a scenic 5k trail around Scoville Reservoir in Wolcott with medals, swag and timed results. Enjoy pre race stretching and free post race yoga, family and dog friendly, with proceeds supporting EndoFound.

Celebrate the Sunday after Thanksgiving at Gorge après Gorge in Chesterfield Gorge with a timed 5k, family fun walk, and new kids race. Finishers earn locally baked cookie medals and a warm postrace potluck to benefit Hilltown Land Trust.

Take on the TARC Winter Classic at Middlesex Fells with 8, 32 and 40 mile Skyline Trail loops featuring roots, climbs and occasional Boston skyline views. Limited spots, cupless aid and winter trail conditions make this a true test for expe..