Trail Running calendar near Union 2025-2026

Powisset Farm Trail Run - Fall invites runners to Powisset Farm in Dover, MA, for a scenic trek through Powisset Farm and nearby Noanet Woodlands. The event offers four distances—8.3, 5.6, 3.1 and 1.5 miles—catering to both experienced trail runners and newcomers. It’s part of the Barn to Run Trail..

RACE FOR THE GREENWAY 5K RUN / WALK takes place at Hallock State Park in Riverhead, NY. The mostly flat off-road 5K course weaves through parkland with views of beaches, vineyards, ponds, and forests, featuring loose gravel and grass underfoot. Runners and walkers of all abilities are welcome.After..

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..

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..

8 Hours at the Farm, held in Brookfield, CT, is a Steep Endurance trail running event on a rolling country course at Gurski Farm/Williams Park. The race features an approximately 4-mile loop with single-track and farm trails, plus options for 8-hour, 4-hour, and 4-mile races. The event emphasizes a..

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..

The Tarckey Trot 6 Hour - Winchester, MA will take place in Winchester on Saturday 15 November 2025. You can run between 6 and 6 kilometers.

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a rugged outdoor event held in Berkley, Massachusetts, honoring military personnel, first responders, and their K-9 partners. Participants can run, ruck with weighted packs, or walk a challenging 5k trail through scenic natural landscapes, often muddy..

Set in Tarrywile Park, Danbury, Connecticut, the Tarrywile Half Marathon offers three distances—10K, Half Marathon, and Marathon—through rugged park trails. The course is renowned for substantial elevation and technical Northeast single-track sections, delivering views of Danbury and the park’s tran..

Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It is the fourth and final race in WTAC’s Fall Trail Race Series, offering two trail distances: 8 miles and 4 miles on Watchaug Pond area trails. Expect a classic, wooded trail course around the pond, with..

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, and hidden ponds, starting near the park entrance off Willi..

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..

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..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course, offering a community-focused a..

TARC Winter Classic is a trail ultrarunning event at the Middlesex Fells Reservation in Stoneham, MA. Runners choose 8, 32, or 40 miles, starting and finishing at Fallon Road. The Skyline Trail offers a rugged New England course of roots, rocks, and elevation, with constant climbs and descents and o..

Tower Tag Challenge is a trail-running event at Sleeping Giant State Park in Hamden, Connecticut. Runners tackle the Tower Trail, a mostly smooth crushed-gravel carriage road that climbs about 600+ feet in 1.5 miles to the park’s Observation Tower, offering views of the surrounding landscape and, on..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5-kilometer race offers participants a chance to escape the roads and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are all welcome, with a requirement of some trail exp..