Trail Running calendar near Winchester 2026-2027

Experience a classic 5k cross country race through the scenic fields of Waters Farm in Sutton. Join the USATF New England Grand Prix season opener on a spike friendly course with both open and masters divisions.

Challenge yourself on a 10-mile loop course through the Big River Management Area in Rhode Island. Choose from 100-mile, 12-hour, or 6-hour ultra distances on a relatively flat trail. All participants receive a race sweatshirt, with a speci..

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Saturday 5 September 2026. You can run 5 kilometers.

Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.

Experience a scenic run through wooded conservation trails finishing at the Hooksett Public Library. This community event features a 5K trail race and a half mile kids fun run to support local youth programs.

This 5K trail run takes participants through the scenic trails and grasslands of Goddard Park in Warwick. The flat course is open to all ages and abilities. Registration includes a T-shirt and ample parking is available.

Experience the natural beauty of Maine by running or walking through woodland trails in Arundel. This conservation focused event offers 5k, 10k, and half marathon distances along with a kids bike race and live music.

Run the Moosup Valley All Trail Race on September 27, 2026. Choose from a 5K, 8K, or 10K on the 100% trail course at Moosup Valley State Park. After the run, enjoy post-race food and a choice of a shirt or medallion.

Run through scenic wetlands and historic military bunkers at the Assabet River National Wildlife Refuge. This cupless trail event offers distances from a 10K to a 6 hour challenge on fast gravel and earth paths.

Experience a scenic downhill course along the shores of Great Bay or take on the virtual 55K challenge. Support local estuary conservation while enjoying a community race that includes a long sleeve shirt and a post race beverage.

Experience a scenic trail run or walk through Ryan Park in Rhode Island to support the North Kingstown Firefighters Association with medals for top age group finishers.

Experience the Bobcat Ridge 25K trail race at the Edwin L Smith Preserve in Maine. This event features a limited field of 100 runners and supports the Kennebunkport Conservation Trust.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

The NipMuck Trail Marathon is a classic 26.4-mile race on Connecticut's rugged Nipmuck Trail. Runners can also team up for a two-person relay. The event supports local trail programs through the nonprofit Shenipsit Striders running club.

Experience the seasonal scenery of New Hampshire at the Keene Family YMCA Fall Foliage Trail Race. Choose between a fast 5K or a 10K with elevation gain to support local community programs.

The Mile for Mentoring will take place in Gilford on Sunday 4 October 2026.

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.

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..