Trail Running calendar near Westport 2026-2027

A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.

A multi event ultramarathon in West Greenwich, Rhode Island featuring a repeated 10 mile loop with desert, pavement and trail sections. Chip timed events include aid stations, a finisher sweatshirt and a buckle for 100 mile finishers.

Timed loop trails on Wachusett Mountain with 7, 14, 21, and 28 mile options over ski slopes and single-track. Participants have 10 hours to finish, with weighted vest options and marked courses; finishers receive a shirt and patch.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

Trail Animals Running Club hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.

A 5K trail run and a 1/4 mile kids fun run at Felix Neck Wildlife Sanctuary in Edgartown, MA, with scenic trails and birdlife. Proceeds benefit the sanctuary's wildlife protection, education, and conservation programs.

A USATF New England Cross Country Grand Prix meet at Great Brook Farm Ski Touring Center in Carlisle, MA on September 13, 2026, featuring a youth 2K and several 5K races across open and masters categories.

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

A one mile obstacle course in Warren, RI with two giant mud pits, kids play area, food and giveaways. Proceeds support Thrive Outside and its programs to expand youth access to nature.

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.

Run for Nature in Lowell on September 27, 2026 features a 10K trail run, a 5K run or walk and a kids one mile fun run, with marked trails and community activities supporting local conservation and education.

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.