Trail Running calendar near Union 2026-2027

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.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

Trail races at Mohawk Mountain in Cornwall CT offer 5K, 10K, Half Marathon and Marathon routes with measured elevation gains, ski area trail loops, cupless hydration policy, and aid stations for longer distances.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

A community running event at the Dighton Rehoboth High School cross country course on October 11, 2026 offering a 5K and a 1 Mile Fun Run with shirts and awards, benefiting Beckwith Middle School athletics.

A 3 mile trail run through Sakonnet Vineyard in Little Compton followed by dinner, wine and music among the vines. Race entry includes timing, a t shirt and a souvenir wine glass; dinner only options are also available.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

Ghost Train Rail Trail Race on October 17–18, 2026 offers races from 7.5 miles to a 30-hour ultramarathon along the Granite Town Rail Trail, with proceeds supporting Brookline and Milford conservation efforts.

A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

A six hour weighted lap race on Mansfield's WWII Veterans Memorial Trail where competitors carry chosen weight each lap and earn Kz by multiplying measured weight by lap distance; the highest Kz in each division wins.

United We Move Trailfest on October 17, 2026 at Fall River Bioreserve offers walk, run, and ride routes of varying lengths to support the Annual Campaign; routes are marked and GPX files are available.

An off road 50k through interconnected woodland preserves in southern Connecticut, featuring rolling forest roads and rocky single track. The event is nonprofit and proceeds support local land conservation, with volunteer roles for aid stat..

Trail races in Wompatuck State Park near Hingham MA featuring a one loop 10 mile and a three loop 50K. Aid stations supply water and snacks and proceeds support Friends of Wompatuck, Free to Run, and Footprints.

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.

A late-October trail race at Mt. Tom State Park with solo and two person relay options on rugged single-track courses, multiple distances, regular aid stations, significant elevation, and proceeds supporting land conservation.

A trail race in Keene, New Hampshire covering 4.9 miles with about 1650 feet of up and down on ski trails and single track. The event benefits the Keene Community Kitchen and includes prize money, age group awards, and raffles.

A fall trail 5k in Berkley MA combining running, rucking, and walking to honor military, first responders, and K9s. Dogs are allowed on leash with a waiver and proceeds support local canine and service organizations.

A fall trail race at Powisset Farm in Dover on October 25 2026 offering four distances, one water aid station, post race cider donuts and family activities with awards for top finishers.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.