Trail Running calendar near Union 2025-2026

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..

Run scenic, hilly single track at the Tarrywile Half Marathon on November 16, 2025 in Danbury CT with 10K, half marathon and marathon options. Rugged terrain, aid stations and finisher medals make for a rewarding trail day.

Run scenic trails around Watchaug Pond at Burlingame State Park with 8 mile and 4 mile options in the Lil Rhody Runaround. Close out the WTAC Fall Race Series while soaking up classic New England fall scenery.

Take on the Baystate Dirty Dog Trail Run Ruck Walk 5k in Berkley on November 16, a rugged, possibly muddy trail where you can run, ruck with a pack, walk, or bring a leashed dog. Proceeds support local beagle and K9 charities.

Run the Brookhaven Trail Half Marathon or 5 Mile through single track, fire trails and sandy woodlands at Brookhaven State Park near Wading River NY. Half marathoners vie for cash, a wood finisher medal and post race refreshments.

Join the Dirty Turkey 5K in Plymouth on Nov 16 for a scenic ocean view run along the Grace Trail, finishing at Historic Cordage Park. Post race enjoy local food, vendors and a complimentary Dirty Water Distillery drink for 21 and over.

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.

Challenge yourself on a hilly 5K at Melrose High School's home cross country course in Melrose, MA while supporting the school's XC teams. Expect rugged terrain, post race snacks, and lively local race day energy.

Join the Novemberfest Race in Nashua for a scenic 4 mile loop through Mine Falls Park, followed by a lively post race party and raffle at Martha's Exchange. Community focused and fun, the event benefits the Nashua Children's Home.

Hit the Brooksvale Trails Turkey Trot at Brooksvale Park in Hamden for scenic 5K and 10K trail runs that are friendly to runners and walkers. Enjoy swag and maple bacon donuts while supporting park trails and a local food drive.

Tackle a rolling 8K through the West Hartford Reservoir at the Hartford Track Club 8K Cross Country Challenge on Nov 23, 2025. Enjoy trails, gravel and scenic views as runners vie for age group honors in a fast, fun fall race.

Join the Roxbury Thanksgiving Charity Race, a scenic 5K in Roxbury, Connecticut, starting and finishing at Everett B. Hurlburt Community Park. Run or walk to celebrate the season and support local causes.

Make Thanksgiving morning active at the Turkeywacker 5K in Wrentham, a festive trail run at Rice Recreation Complex with donuts, cider and raffle prizes. Awards for top finishers across ages ensure competition and family fun.

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.

Celebrate Thanksgiving on the trails at the F.I.T. Turkey Trot Trail Race in Cumberland, Rhode Island on November 27. Choose from 5K, 5 Mile, combo, multilap or a Kids Race and earn a unique finisher medal.

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.

Join the Tower Tag Challenge at Sleeping Giant State Park for a scenic timed loop to the Observation Tower, with 4 hour and 8 hour options. Run repeated 3.3 mile laps on a smooth carriage road with aid station support and finisher medals.

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..

Run the Frosty Forest 5K in Stratford through Roosevelt Forest on an off road trail welcoming runners, joggers and walkers. Holiday costumes encouraged, every finisher gets a commemorative item and proceeds support local charities.