Trail Running calendar near Roxbury 2025-2026

Join the 9th annual Fall Back into the Trails at Red Wing Recreation Area in Lagrangeville NY for two days of scenic, supported loop trail racing with 10K 50K and 100K options. Custom finisher medals, camping and UTMB index for longer races..

Run through the vines at Stonington Vineyards in this chip timed 5k that finishes with a wine pour, unique finisher medal, and a shatterproof wine glass. Two laps through scenic vineyard trails make it perfect for runners and walkers.

Overview 8 Hours at the Farm is a timed trail running event presented by Steep Endurance on November 2 in Brookfield, Connecticut. The event is held at Gurski Farm / Williams Park with race headquarters and the start/finish located in the b..

Event information The People in Need - Day of the Dead 5K is scheduled for Sunday, November 2, 2025, in Fresh Meadows, New York. The event is a charity 5K walk/run organized to raise funds and awareness for People in Need. The event locatio..

The Veterans Day Cross Country 4K Run, hosted by the Northport Running Club, is held at the Veterans Administration Medical Center Golf Course in Northport, NY. The English-style 4K course runs entirely on grass (about 2.48 miles) with no p..

Choose Marathon or Half Marathon on a single loop through Rockefeller Preserve, a rolling hilly course with Hudson River and Palisades views amid fields, forests and stone walls. Proceeds support local conservation groups.

Event overview The Beacon Bonfire 10K takes place in Beacon, NY on Saturday, November 8, 2025. The event is a 10K trail race that starts and finishes at the Mt Beacon Trailhead. Registration closes Thu, Nov 6 at 11:59 PM ET. The race has a..

Raven Rocks Run (10k) at Ward Pound Ridge Reservation The Raven Rocks Run is a trail event held at Ward Pound Ridge Reservation in Cross River, NY. The in-person event includes a 10k trail run that climbs to the park's high points, passing..

The Centerville Bank Thompson Turkey Trot is an annual event held at the West Thompson Dam Overlook Shelter in Thompson, Connecticut. It features a 5K timed trail run, a 3K untimed walk called the "Wobble" where dogs on leashes are welcome,..

Taconic Road Runners FDR Park Cross Country Run is a cross-country race held in Yorktown Heights, New York, at FDR Park. The event features a 6K course that includes almost two miles of the park’s trail system, with most of the route on sof..

Run the Never Stop Running Foundation Long Island Turkey Trail Trot, a scenic 5K through Bethpage State Park on Nov 15, 2025. Family friendly with a kiddie dash and proceeds benefiting local youth and athlete development.

NJ Trail Series SOMO Winter 1 is a trail running event held in South Orange, New Jersey, at South Mountain Reservation, with distances of 5K, 10K, and 13.1 miles on a looped course. The route blends fire roads, single-track, hills, and some..

Located in Brookhaven State Park, Wading River, NY, the Brookhaven Trail Half Marathon and 5 Mile offer two trail-running distances. The course traverses a mix of Suffolk County woodlands, including single-track, fire roads, sandy sections,..

Event details The Tarrywile Half Marathon is a trail running event held on November 16 at Tarrywile Park, 70 Southern Blvd., Danbury, Connecticut. The event offers three distances: Marathon Half Marathon 10K Registration tiers vary by dat..

Event details Fall Fling 400 is organized by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut on November 22, 2025. The event offers two main entry options: 400-minute run on a roughly two-mile loop 4 Mile (two laps of th..

Brooksvale Trails Turkey Trot : November 23, 2025 The Brooksvale Trails Turkey Trot takes place in Hamden, CT, at Brooksvale Park (524 Brooksvale Avenue). The event is organized by Live Loud Running and the Town of Hamden and is the third a..

Join the Roxbury Thanksgiving Day Charity Race for a festive 5K through Everett B. Hurlburt Community Park. Support local causes and burn off holiday calories with friends and neighbors this Thanksgiving morning.

NSRF Leftover Turkey Trot 5K at Bethpage State Park (Polo at the Park) offers a 5K Run/Walk on grassy polo-field and scenic trails, with mostly flat, beginner-friendly terrain and some rolling sections reminiscent of cross-country. The even..

Event details The Squatchy Leftovers is a trail race on Saturday, November 29, 2025, at South Mountain Reservation, 374 Walker Road, West Orange, NJ. Distances offered include: 50K - 10 loops 25K - 5 loops 10K - 2 loops 5K - 1 loop 1 Mile..

Join the Never Stop Running Foundation 50/50 Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30. Half of net proceeds are raffled to participants with winners present and the rest supports the foundation.