Trail Running calendar near Medford 2026-2027

Survival of the F.I.T.test is a 30 hour trail ultra held in October as part of the F.I.T. Challenge calendar in Cumberland, Rhode Island. Results for past editions are published online after each race.

A virtual 55K challenge linked to the Great Bay 5K in Stratham, New Hampshire. Complete 55 kilometers in one day or between October 1 and October 24, 2026; registration includes a shirt if ordered by October 1 and a bib with a beer or cider..

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..

Experience an old school trail race along the historic Nipmuck Trail in Connecticut. This 26.4 mile double out and back event follows the blue blazed trails through challenging New England terrain.

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.

A UTMB Index point-to-point trail event in central New England offering 100 Miler, 50 Miler and 50K options that follow the marked Midstate Trail across multiple states. Wave starts and seeded pacing manage aid station support.

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..

Vulcan's Fury Trail Race at Pawtuckaway State Park offers a half marathon and a 5 Miler over technical trails with boulder fields, switchbacks, stream crossings and a rocky ridge called the Devil's Staircase. Three aid stations support runn..

A community 5K and 1 Mile Fun Run on 10/11/2026 at the Dighton Rehoboth High School Cross Country Course in North Dighton, MA. Proceeds support Beckwith Middle School athletics and the Beckwith Believers student athletes.

The Wine Run offers a scenic 3-mile trail run through Sakonnet Vineyard. After the run, participants enjoy dinner, wine, and live music on-site. The event also includes non-running dinner options for adults and children.

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.

Experience New Hampshire’s original 30 hour ultramarathon on the historic Granite Town Rail Trail. Choose from multiple distances and relay options in this flat and fast Halloween themed fundraiser for local trail conservation.

A six-hour weighted lap race on the WWII Veterans Memorial Trail in Mansfield, MA, where distance is multiplied by the weight carried to score "Kz" pound-miles; competitors may change weight each lap and aim for the highest total.

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.

Join a community trail race through the diverse terrain of Wompatuck State Park. Choose between a ten mile loop or a 50K distance on a course featuring rail trails and single track paths.

Run a scenic autumn 5k trail through Wrentham conservation land and a working farm. This cup-less race supports local agriculture and includes family Halloween fun. It's the final event of the Farm to Trail 5K Series.

Fall trail races on rugged single-track at Mt. Tom State Park include a 25k, 2-person 25k relay, 10k and a 5k fun run with significant climbing and proceeds benefiting Kestrel Land Trust.