Trail Running calendar near Manchester 2026-2027

A forested 5K on the new trails at Bridgewater Town Park in Bridgewater, CT. The 3rd annual event features mixed natural terrain, views of Lake Lillinonah, participant gifts and awards for top finishers.

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 multi day timed trail event on a Winchendon farm using a roughly two mile loop. Runners choose from six hour day or night, 12 hour, 24 hour, or 48 hour formats under the Sturgeon Moon.

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..

Trail races in Fahnestock State Park near Cold Spring, NY, offering 50K, 25K and a 5.5-mile course on varied terrain with on-course support, post-race meal, and proceeds supporting land conservation.

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 6 hour timed ultra and a 4.2 mile memorial run at Jug End State Reservation in Egremont MA on August 22, 2026. The loop covers woods and orchards with 830 feet elevation per lap and benefits Louison House and Dana Farber.

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.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

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.

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

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.

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.

A trail race day at Pittsfield State Forest with 50k, 25k, 15k and a new 5 mile option, a double-loop course with three aid stations and charity fundraising through BURCS and Free to Run.

Trail race at Macedonia Brook State Park in Kent, Connecticut on September 13, 2026. Courses of 12K, 25K and 50K on single track forest trails with steep climbs, technical sections and cupless aid stations.

Trail races in Pisgah State Park near Chesterfield, New Hampshire offering 50K and 23K distances, organized by the Red Clover Rovers as a fundraiser for the Special Olympics of New Hampshire.

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.