Trail Running calendar near West Greenwich 2025-2026

Join the 8th Annual Taco Trials in Rocky Hill: eat a taco then run a 1 mile loop, repeating it ten times for a fun, quirky challenge. Medals for finishers and proceeds benefit the Connecticut Forest and Park Association.

Seth's Fat Ass 50K at Forest Park in Springfield is a friendly challenge of up to ten 5K loops. You have seven hours to run as many laps as you like, grab event schwag and a t shirt, and enjoy the social ultrarunning vibe.

Run winter trails at Powissett Lodge in Westwood MA on Feb 7 and 8 2026 with a 30 hour ultra or a 15 mile loop. Enjoy a marked three loop course, aid at the lodge, and help support local land conservation.

Join Ramsey's Run, a scenic 5k trail run through the woods in Kingston MA on Saturday March 14, 2026. This memorial event honors a Class of 2023 student and raises funds for a scholarship established by the family.

Run or walk a scenic 5k through the rolling vines at Osprey's Dominion Vineyards in Peconic. Enjoy two laps of cross country terrain, a finisher medal that doubles as a bottle stopper and a postrace wine pour among the vines.

Join Trail Animals Running Club at Hale Reservation for a scenic trail challenge featuring a 3.5 mile loop or a timed 6 hour option. Expect technical singletrack, pond shorelines, boardwalks and a friendly aid station; bring your own cup.

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

Take on rugged singletrack, a steep headwall scramble and 3,000 feet of climbing at Sleeping Giant Trail Runs, with 25K and 50K options. At Sleeping Giant State Park in Hamden CT on March 29, proceeds benefit the park and finishers get meda..

Run Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.

The Merrimack River Trail Race is a USATF-sanctioned 10-mile out-and-back trail run held in Andover, Massachusetts, starting from the DoubleTree by Hilton Hotel parking lot. The course features water stations at miles 2, 4, and 8, with a mi..

Spring Fever brings scenic early spring trail racing to Wompatuck State Park in Hingham on April 11, with 5K, 5 mile, and an 8 hour multi lap challenge. Expect muddy trails, on course aid, and a friendly campground finish line vibe.

Run a scenic 6.55 mile quarter marathon through West Hartford Reservoir 4 as two loops around the park. Limited to 150 runners, the event features chip timing, post race treats and awards in five year age groups.

Take on the rugged Traprock trail at Penwood State Park with a single 17K loop or three loops for the 50K for a true trail challenge. Expect rocky, technical single track, rolling terrain and great forest views.

Run the scenic trails of Jericho Town Forest in Weston, MA with distances from 10K to 50K on a fast, smooth loop. Welcoming to youth, adaptive athletes, and volunteers; note the event is cupless so bring your own hydration.

Blue 2 Blue Challenge is a demanding 50K on May 3, 2026 in New Haven, Connecticut, across rugged blue blazed trails with steep, technical climbs. Entry is by waitlist and requires a recent qualifying trail 50K, so come prepared.

Run the scenic Dandelion Dash 5K on The Hartsbrook School trails or enjoy the family friendly Mushroom Mile in Hadley, MA. Support school programs in sustainable agriculture and beekeeping or run virtually from anywhere.

TARC Wapack and Back is a scenic, rugged trail race in May on the Wapack Trail between Massachusetts and New Hampshire, offering 21.5, 43 and 50 mile options. Expect technical terrain, big climbs, limited aid, and a tight knit trail communi..

Experience the 9th annual Wildcat 5K Trail Run, Walk and Wag on May 30, 2026 in Boxford, a scenic 5K around Stiles Pond through Wildcat State Forest. Runners, walkers and their dogs will enjoy trails, prizes and a festive post race celebrat..

Run or ride scenic farm trails at Norbrook Farm Brewery in Colebrook CT, with options from a 5K and 10K to a 4 hour trail challenge, duathlon and competitive mountain bike races. Finishers get custom medals and entrants 21 plus receive a fr..

Take on a scenic 15.7 mile trail run on the Nipmuck Trail in Mansfield CT, following the Fenton River through woods, fields and small bridge crossings. Organized by the Shenipsit Striders, proceeds support local trail stewardship.