Trail Running calendar near Winchester 2025-2026

The North Kingstown Firefighters Association Blazing Trail 5K is a first-year fall trail run/walk held at Ryan Park in North Kingstown, Rhode Island. The 5K course follows a scenic park trail, welcoming runners and walkers of all ages and e..

Event overview The Bobcat Ridge 25k is a 25k trail race held on the trails of the Edwin L. Smith Preserve in Kennebunkport, Maine. The event takes place on Saturday, October 4, 2025, at the Edwin L. Smith Preserve Trailhead on Guinea Road...

Keene Family YMCA Fall Foliage Trail Races in Keene, New Hampshire offer 5K and 10K trail runs starting and finishing at the Keene YMCA (200 Summit Road). The 5K provides a fast, beginner-friendly taste of trail running, while the 10K adds..

NipMuck Trail Marathon in Ashford CT offers 26.4 miles of rugged singletrack with rocks, roots, mud and wood bridges. Run solo or in a two person relay and help support Connecticut trail stewardship.

Groton Town Forest Trail Races, held at 163 West Main Street, Groton, MA, offer two trail distances: 9.5 miles and 3.4 miles. The courses are well-marked and feature a scenic loop through Groton Town Forest with no road crossings, combining..

Stairs4RTroops 2025 at Gillette Stadium in Foxboro, Massachusetts is a stair climb, walk, or run up the stadium stairs and around the lower concourses. Held on October 5, 2025, the event features multiple waves roughly every 15 to 30 minute..

Event Trust Trail Fest takes place on October 5, 2025 at the Kennebunkport Conservation Trust headquarters, 57 Gravelly Brook Road, Kennebunkport, ME. Participants can choose a trail 5k or 10k course that winds through the KCT trail system..

The Houghton's Pond Trail Races take place in the scenic DCR Blue Hills Reservation in Milton, Massachusetts, just south of Boston. This event offers two trail race distances: 7 miles and 3.7 miles, both starting and finishing near the Houg..

Tackle the Midstate Massive Ultra Trail, a point to point autumn ultra across New England with 100 mile, 50 mile and 50k options. Routes wind through mountains, fields and rivers along the historic Midstate Trail for a true adventure.

The Wayland / HFC Striders XC Festival, held in Wayland, Massachusetts, is a vibrant cross-country running event featuring three youth 3K races and two open 5K races for adults. The course winds through scenic fields and wooded trails, offe..

Run rugged trails amid peak New Hampshire foliage at Vulcan's Fury in Nottingham NH on Oct 12, 2025. Half marathon and 5 Miler courses feature boulder fields, steep switchbacks and scenic stream crossings for a true fall trail test.

ORR Alumni Trail Race is a 5k run/walk held in Marion, Massachusetts, on the Washburn Park cross-country course. The event invites supporters to back the Old Rochester Regional cross country and track and field teams, with all proceeds dire..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.

United We Move is an annual trail event held in Fall River, MA, set within the scenic Fall River Bioreserve. Participants can choose from multiple distances and activities, including a 20-mile and 10-mile gravel bike ride, 10-mile and 5K ru..

Carry your chosen load and tackle the 2.5 mile out and back on the WWII Veterans Memorial Trail in Mansfield, aiming to complete as many laps as you can in a six hour window. Each lap adds to your pound mile score for overall placement.

Mt. Tom Trail Race The Mt. Tom Trail Race takes place on October 18, 2025, with the start/finish and parking at Bray Lake in Mt. Tom State Park. The event is a nonprofit fundraiser that supports the Kestrel Land Trust. Registration fees are..

Run under peak autumn foliage along the haunted Granite Town Rail Trail in Brookline, NH, with options from 7.5 miles to a 30 hour ultramarathon. All profits support local conservation as the trail comes alive in October.

The Ravenswood Trail Race, part of the North Shore Trail Series, takes place in Ravenswood Park, featuring a scenic course through single track and carriage roads amid peak fall foliage. This classic fall trail race offers a challenging and..

The Weir River Farm Trail Race, held annually in Hingham, Massachusetts, offers runners three trail distances: 10 miles, 6 miles, and 3.4 miles. The race courses wind through the scenic trails of Weir River Farm, Whitney, and Thayer Woods,..

Book It for Books 5k & 10k is a charity running event at Lake Accotink Park in Springfield, VA, benefiting Reading is Fundamental of Northern Virginia (RIF NOVA). The weekend features a 1-mile fun run, a 5k trail out-and-back on the lake’s..