Trail Running calendar near Hadley 2025-2026

Cheshire Community YMCA 5K Harvest Trail Run in Cheshire, CT, is a race around Ives Farm. The all-ages event winds through fields and trails on the farm, starting and finishing at the remodeled barn. Proceeds support the YMCA’s Cheshire community programs and the Cheshire Land Trust’s revitalization..

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 south side, and a 10k course that runs out-and-back on the n..

Pumpkin Pacer 5k @ White Barn Farm is a 5K off-road trail run/walk held at White Barn Farm, 431 South Street, Wrentham, MA 02093. It’s the final race in the Farm To Trail 5K Series and is open to all ages and abilities. The course weaves through scenic conservation land and farm property, featuring..

Run for the Hills in Harvard, Massachusetts is a pair of off‑road trail races held at the Community Harvest Project Orchard (115 Prospect Hill Rd). The event features a challenging 5K trail run through orchard, woods, and fields, plus a 1‑mile kids’ fun run staying within orchard trails. The course..

The Powisset Farm Trail Run - Fall takes place on Sunday, October 26, 2025, at Powisset Farm, 37 Powisset Street, Dover, MA. The event is part of the Barn to Run Trail Race Series and uses trails at Powisset Farm and neighboring Noanet Woodlands. The race features multiple distances and includes po..

New Boston, NH hosts The Hamsterwheel, an 11th-year ultrarun along the New Boston Rail Trail by the Piscataquog River. The course is a continuous 4.0-mile loop that is largely flat with one minor speed bump, starting near the Hillsborough County Fairground and turning at Lang’s Station. Runners may..

Fall Back Into The Trails Series returns to Red Wing Recreation Area in Lagrangeville, NY for its 9th annual edition on November 1-2, 2025. The event offers three races: 100k (10x10k loops with about 1,000 ft of gain per lap), 50k (5x10k loops with about 5,000 ft total gain), and 10k (about 1,000 ft..

The Hugs from Vets Trail will take place in Henniker on Sunday 2 November 2025. You can run 10 kilometers.

The Saratoga Stryders Fall Back 5 Mile Trail Race is held annually at Saratoga Spa State Park in Saratoga Springs, NY. This challenging 5-mile course features a mix of hills, ridges, single-track trails, wide paths, paved sections, grassy areas, and even a stair climb near SPAC, offering runners a d..

8 Hours at the Farm is a trail running event by Steep Endurance in Brookfield, Connecticut, on the rolling grounds of Gurski Farm/Williams Park. The race features approximately a 4-mile loop weaving single-track and farm trails, delivering a rolling, not-too-technical course and a supportive trail-r..

Stonington Vineyards hosts the Wine Run Turkey Trot 5k at Stonington Vineyards in Stonington, CT. This timed 5k offers a run or walk on a two-lap cross-country course that begins and ends at the winery, weaving through vineyard lanes with occasional uneven footing. The atmosphere blends fitness with..

Race for DFL is a last-runner-standing backyard ultra held at Kenty’s Farm in Winchendon, Massachusetts. The event uses a single lap of about 4.17 miles, with a course mixture of grassy field, forest trail, crushed gravel bike path, and a dirt road, totaling around 150 feet of elevation gain per lap..

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, and a free kids' fun run for children 12 and under. The eve..

Located in Upton State Forest, Upton, MA, the Upton 10.5K and Half Marathon Trail Race offers two trail options: a 10.5K and a half marathon run as two laps on technical, hilly single-track trails and forest roads. Each lap is about 6.5 miles with roughly 720 feet of elevation gain. The course featu..

TARCkey Trot 6 Hour at Wright Locke Farm in Winchester, MA is a six-hour trail race on a 5K loop. Laps feature rocky, rolling terrain that rewards focus, with runners choosing how many to complete within the time limit. The course is clearly marked with flagging and signs; a GPX file is available, a..

Set in Tarrywile Park, Danbury, Connecticut, the Tarrywile Half Marathon offers Marathon, Half Marathon, and 10K trail distances. The course is renowned for its toughness, with close to 3,000 feet of elevation and substantial Northeast single-track, featuring rocky, rooty, and hilly terrain. The rou..

Fall Fling 400, the CT Trailmixers’ ninth annual trail race, takes place at YMCA Camp Sloper in Southington, CT. The event offers two options: Fall Fling 400, where runners complete as many roughly two-mile loops as possible within a 400-minute limit (roughly 28 miles minimum), and the Spring Fling..

Mount Ascutney Vertical Backyard, in Brownsville, Vermont, is a Last Person Standing endurance race on Mount Ascutney. Runners ascend and descend the mountain hourly, with two ascent options: a three-lap orange loop up the t-bar path for 403 vertical feet per lap, or a single ascent on the green loo..

The Novemberfest Race for the Nashua Children’s Home is a festive 4-mile run through Mine Falls Park in Nashua, New Hampshire. The course takes runners through the scenic Mine Falls Park with the start/finish area near the Pine Street Extension entrance, just west of the Millyard Smokestack. After t..

Turkeywacker 5K is a Thanksgiving morning trail run held in Wrentham, Massachusetts, at the William Rice Recreation Complex (54 Emerald Street). Now in its ninth year, the scenic 5K course winds through the complex’s trail system, welcoming runners and walkers of all ages. After the race, participan..