Trail Running calendar near West Greenwich 2025-2026

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..

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..

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..

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..

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 TARC Winter Classic is a trail-running event staged at Middlesex Fells Reservation in Stoneham, Massachusetts. Runners choose among 8, 32, or 40 miles on the Skyline Trail, a challenging route of roots, rocks, and elevation with classic New England forest scenery and occasional views of the Bost..

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 Mount Hood Nutcracker Challenge is an annual cross-country running event held at the Mount Hood Golf Club in Melrose, Massachusetts. This unique 3.5-mile race features a challenging, hilly course that changes every year, incorporating fairways, paved cart paths, road crossings, and wooded sectio..

TARCtic Frozen Yeti takes place at Hale Reservation in Westwood, MA, with a 15-mile loop and a 30-hour ultra option. The course is a tri-loop layout centered on a heated lodge at Powissett Lodge, with three roughly five-mile leaves marked by color-coded loops; runners can complete a single 15-mile l..

The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is chip timed and scored by J3 Timing; results will be posted online at J3Timi..

Located in Union, Connecticut, the Northern Nipmuck Trail Race is a 16-mile ultramarathon staged just outside Bigelow Hollow State Park. The course runs south on the Nipmuck Trail through the Yale-Myers Forest, crosses Barlow Mill Rd at mile 4, then reaches a turnaround at Boston Hollow before retra..

Sleeping Giant Trail Runs, hosted by Steep Endurance at Sleeping Giant State Park in Hamden, CT, offers challenging 25K and 50K trail races through Connecticut’s iconic park. The 25K loop features more than 3,000 feet of vertical gain across rocky and rolling singletrack via Yellow, Chestnut, White,..