Trail Running calendar near Charlton 2026-2027

A backyard ultra at Kenty’s Farm in Winchendon MA on November 7, 2026 where runners repeat 4.1666 mile laps until one remains. The event also offers 6, 12 and 24 hour timed options plus a single lap competition.

A looped trail event at White Barn Farm in Wrentham, MA on Nov 7, 2026, featuring 3.1 mile laps on grass and dirt. Distances range from 5K to 50K so participants can choose how many laps to run.

A Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.

Trail races in Upton State Forest include a 10.5K loop and a 13.1 mile half marathon run as two laps. Aid stations are spaced about every 3 miles and post race offerings include fire pits, hot soup and hot chocolate.

Push your limits on the scenic wooded trails of Wright Locke Farm with the TARCkey Trot, a 6 hour timed event run on a repeated 5K loop. Bring your own cup and register online early as day of registration is not offered.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

A trail event at YMCA Camp Sloper on November 21, 2026, offering a 400 minute timed loop option and a two mile two lap race, with chip timing, a central aid station, and proceeds supporting local organizations.

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 community Thanksgiving event featuring a 3.5 mile run and walk around Scoville Reservoir in Wolcott CT, with multiple start waves, post race yoga for participants, finisher medals, volunteers supporting refreshments, and proceeds to EndoF..

A trail running event at Middlesex Fells Reservation with **8 mile**, **32 mile**, and **40 mile** loop options on the white blazed Skyline Trail. The course is technical and minimally marked, cupless with two aid stations and specific cour..

Repeat a 3.3 mile out and back up the Tower Trail to the Observation Tower at Sleeping Giant. Runners choose a four hour or eight hour format, carry their own hydration, and complete as many laps as they can within the time limit.

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.

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.

A spring trail out-and-back on the Nipmuck Trail near Bigelow Hollow, advertised as 16 miles on technical, blazed singletrack with minimal aid and limited parking; proceeds support local trail stewardship.

A 123-mile point-to-point ultramarathon across Connecticut combining roughly 57 miles of trails with paved backroads, a 36-hour cutoff, relay options, aid stations, on-course medical support, and finish awards including a buckle and event s..

Trail races at Sleeping Giant State Park in Hamden, CT offering 25K and 50K loops. The 25K has 3,000 plus feet of vertical gain and varied terrain from carriage roads to steep rock scrambles, with aid stations and postrace food available.

The TARC Spring Classic takes place April 24, 2027 in Jericho Town Forest, Weston, MA, with 10K, half marathon, marathon and 50K looped trail options, a single aid station, marked course, and a cupless race format.