Trail Running calendar near Kingston 2026-2027

A memorial 5k trail run and walk in Kingston, MA on March 14, 2026 that raises funds for a scholarship established by the participant's family. First fifty entries receive a t-shirt and all proceeds support the scholarship.

A Trail Animals trail event at Hale Education in Westwood offering a timed six hour option and a 3.5 mile singleloop on mostly singletrack around ponds. One cupless aid station at start/finish and limited parking with possible walking.

A classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

The Tortoise and the Hare Trail Races feature a timed 10K, 5K, and a fun 1-mile color run in Salisbury, MA. This annual fundraiser for local parks draws a crowd of about 500 participants. Runners can enjoy trail courses, post-race refreshme..

This USATF-sanctioned 10-mile trail race runs along the Merrimack River in Andover, MA. The event features unique homemade prizes and awards, with proceeds supporting local trail maintenance. Post-race refreshments and a raffle add to the c..

Shake off winter at the Spring Fever trail run in Wompatuck State Park. Choose from a 5K, 5M, or 8-hour ultra on a reversed course. All finishers get a custom award and can enjoy on-course support.

A trail race at Jericho Town Forest (Weston, MA) on April 25, 2026 offering 10K, half, marathon, and 50K options on a marked 10K loop, cupless aid station, strict cutoffs, and parking by volunteers.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

The Radish Rambler 5k is a trail run, walk, or hike through scenic conservation land and White Barn Farm in Wrentham. Held on April 25, 2026, it kicks off the farm's season and the Farm to Trail Series. Proceeds support local agriculture an..

The Rescue Run: Race for Marine Mammals will take place in Rye on Saturday 2 May 2026. You can run 5 kilometers.

Explore the trails at the scenic Frances A. Crane Wildlife Management Area. Choose your challenge with 10K, 20K, or 30K looped courses. This event supports local conservation and community wellness initiatives.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

The Watuppa Trail Races offer a fast and flowy course through the scenic Watuppa Reservation. Choose from three distances: a 10K, 30K, or 50K. The event is known for its community feel and welcoming finish line.

Experience the varied landscapes of Block Island with a 10K course featuring coastal tracks and rolling pastures. Running through diverse terrain this spring event includes a steep double tiered climb and views of the Atlantic.

A point-to-point 50-mile ultramarathon from Manchester to Monadnock State Park, featuring over 6,000 feet of elevation gain. The course mixes roads, dirt roads, and trails, and requires GPX navigation. With limited spots, runners must plan..

The Trav's Trail Run will take place in Newburyport on Sunday 17 May 2026. You can run 3 miles.

Run a unique 4K trail race on Cathleen Stone Island in Boston Harbor, accessed by a short ferry ride. The two-day event supports free science education for local youth and features a post-race party. Choose to run individually or with a cor..

This spring trail run on May 25, 2026, takes you through the scenic paths of Powisset Farm and Noanet Woodlands in Dover, MA. Choose from four distances, from 1.5 to 8.6 miles, in this cupless race. It's part of a farm-based series with awa..

Run or walk through the scenic Wildcat State Forest Trail in Boxford. This bird friendly event features separate courses for runners and walkers starting at the Danvers YMCA Camp overlooking Stiles Pond.