Trail Running calendar near Tolland 2026-2027

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

The Arc'teryx Run Boston will take place in Milton on Sunday 20 September 2026. You can run 10 kilometers.

A 5K trail run at Goddard Park in Warwick, RI on September 26, 2026, with a bayside course and start and finish near the golf course clubhouse. Open to all ages, with published entry fee tiers and on site parking and facilities.

An all-trail event on the Moosup Valley State Park Trail in Moosup, CT offering 5K, 8K, 10K and a free Kids Fun Run with post-race shirts or medallions and food at Weidele's; proceeds benefit a local Rotary charity.

Trail races at the Assabet River National Wildlife Refuge in Sudbury MA include a 10K, a 30K and a 6 hour timed event. The course uses dirt and gravel double track trails with two aid stations and cupless fueling.

A community run at Shedd Park featuring a 5K, a 10K trail run, and a 1-mile kids fun run, with educational displays and proceeds supporting LP&CT's conservation and education programs.

Experience a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

A 24 hour trail event at Mohawk Mountain Ski Area in Cornwall Connecticut featuring a Double Kuwohi route of about 28 miles and 13,685 feet of elevation. Participants may run, hike, or walk.

A 30 hour loop ultra at Roosevelt Forest in Stratford CT on a 2.23 mile course with roots, rocks and a notable hill. Field limited to 50 runners; completing 45 loops within 30 hours earns a finisher buckle.

Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.

A 5K fall trail run and walk at Ryan Park in North Kingstown on October 3, 2026, benefiting the North Kingstown Firefighters Association. Registrations before September 14 include a race day t shirt and top finishers receive medals.

A timed trail ultra in Cumberland RI offering 8 hour, 12 hour, and 34 hour options for individuals and teams up to four. The 4.2 mile loop mixes smooth trail and moderately technical rocky sections.

Trail races in Groton, Massachusetts on October 4, 2026, organized by local running and trails groups. Two distances, 9.5 miles and 3.4 miles, total entries limited to 250, online registration closes October 3.

Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.

A 26.4 mile trail marathon on Connecticut’s Nipmuck Trail featuring rocks, roots, mud and wood bridges, with an optional two-person relay and elapsed time cutoffs. Organized by the Shenipsit Striders in Ashford, CT.

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.

Trail races at Houghton's Pond in the DCR Blue Hills Reservation follow rolling dirt roads and forest paths with rocks and roots. Two distances are offered, about 7 miles and 3.7 miles, with notable elevation change on each course.