Trail Running calendar near Pawcatuck 2026-2027

A 12K trail race on the Blue Hills Skyline Trail with about 2,300 feet of climbing, rocky steep terrain, and minimal aid. The route follows Skyline blazes from the Blue Hills Ski Area parking lot and requires participants to carry hydration..

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

A one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

A 5.5 mile trail race at Soapstone Mountain with six ascents and about 1500 feet of climb. The field is capped at 50 runners for parking reasons and online registration is required.

A 5K mud run on August 1, 2026 at 508 INTL- Adventure Sports Center in Boston, featuring obstacles, mud pits and slides, plus Pre-Party and After-Party with music, food and beer. Kids are welcome and light quick-dry gear is recommended.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.

A seaside set of timed ultra-marathon events at Colt State Park in Bristol, Rhode Island, offering 6 hour, 12 hour, and 24 hour formats with separate entry periods and fees.

TARC Summer Classic at Noon Hill Reservation features a mostly forested 10 mile loop with singletrack, gravel and a scenic vista. The event offers 10 mile, 50K and 40 mile options and includes mandatory trail briefings and finish time limit..

The Running Wild at Wildwood Trail 2.5 Mile Trail Run/Walk will take place in Wading River on Saturday 8 August 2026. You can run 3 miles.

Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.

A community running event in Tolland, CT featuring a marked 5K trail loop run repeatedly over an eight hour period, potluck food and grill items, raffle tickets awarded per loop, and a 50th anniversary gift for runners who complete at least..

A scenic off-road 5K at White Barn Farm through conservation land with a midway water station and marshaled course. Proceeds support the farm and a donation to the local food pantry.

A timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.

A 5K cross-country race at Waters Farm in Sutton, MA, marking the fourth running of the Old Goat Track Club XC Classic with on-site parking, finish-line water and fruit, portable toilets, and awards for individual and team results.

Ocean State Ultra in West Greenwich, Rhode Island (August 29–30, 2026) offers a 100 mile race with a 34 hour limit plus 12 and 6 hour loop events; registration runs March 30 to August 17, 2026.

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.

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.

Sterling Down & Dirty 5K is an annual family friendly obstacle race on Stratford Short Beach each September. Participants tackle more than 18 obstacles, join teams to fundraise for the Sterling Community Center, or volunteer on race day.

A group, end-to-end run along the Farmington Canal Heritage Trail from West Suffield to New Haven, roughly 56 miles, raising funds for Mental Health Connecticut. The route is largely flat and unsupported with a 14 hour completion cut off.