Trail Running calendar near Southwick 2026-2027

Run or walk a 5K through the scenic Osprey's Dominion Vineyards in Peconic. Registration includes a wine glass, a medal that works as a wine stopper, and a pour of wine. The event is open to all ages and even welcomes leashed dogs.

A low key out and back trail race in Union, Connecticut, following the Nipmuck Trail for about 16 miles of technical, hilly terrain with minimal aid stations and a cap of 100 runners. Proceeds support local trail stewardship.

A trail race at Sleeping Giant State Park in Hamden, CT, built on a 25K loop with a 50K two-loop option. The course features technical singletrack, steep scrambles and an ascent to the Observation Tower.

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

The Bimbler's Bash is a popular annual 10K trail run through the technical, rocky paths of Guilford's Westwoods. This entirely off-road event supports local land conservation and is known as a major single-distance race in Connecticut.

Run a unique *6.55-mile* quarter marathon on the scenic paved trails of West Hartford Reservoir. This small event, limited to 150 participants, features two loops and professional timing. Race day registration is available with a $25 cash f..

A USATF certified point to point half marathon in Albany County on April 11, 2026, mostly on paved rail trail with a net downhill and a 500 foot elevation drop to a Hudson River finish. The event offers live tracking, bus to the start, post..

A community trail event in Cross River, NY on April 12, 2026 featuring a 5k trail race, a 4k walk that skips part of the hill loop, and a 200 meter kids dash on the track.

Trail races at Penwood State Park offer a 50K (three loops) and a 17K (one loop) over primarily single-track and double-track terrain, with a nine hour cutoff for the 50K. The event is cupless and organized by the CT Trailmixers.

Run or walk a 5K through the orchards of Brooklyn Cider House. Registration includes a cider glass, donut, and finisher medal. The event is open to all ages and welcomes dogs and strollers.

Two trail races on April 19, 2026 at Brookhaven State Park in Wading River: a 15K and a 4 mile course through single track, fire trails, sandy sections and woodlands, run as a cupless event with age group awards and charity support.

A trail race at Jericho Town Forest (Weston, MA) on April 25, 2026 offering 10K, half, marathon, and 50K options on a marked 10K loop, cupless aid station, strict cutoffs, and parking by volunteers.

A women’s-only trail running event at Lake Mohegan in Fairfield offering a runnable 5K loop, 10K, and a 4 hour looped challenge; the race includes finisher medals, top-3 awards, post-race refreshments, and a cupless sustainability policy.

A 15K trail race at Grafton Lakes State Park covering about 9.3 miles with 900 ft of elevation gain. The technical yet runnable spring course can be muddy and is described as accessible for new trail runners.

A three-race 5K series at White Barn Farm in Wrentham, MA, held across spring, summer and fall. Each trail event reflects seasonal conditions and a Grand Prix combines results for awards and a gift bag at the final race.

The Radish Rambler 5k is a trail run, walk, or hike through scenic conservation land and White Barn Farm in Wrentham. Held on April 25, 2026, it kicks off the farm's season and the Farm to Trail Series. Proceeds support local agriculture an..

Leatherman's Loop is a 10k trail race at Ward Pound Ridge Reservation in Cross River, NY on April 26, 2026. Entry is by lottery and the race is USATF sanctioned; registration includes the park entry fee.

A 12 mile out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.

A Run to Remember in Red Hook NY features 5K and 10K trail races plus a 5K walk on May 2, 2026. Courses run through meadows, forest, orchards and berry patches and cash prizes are awarded.

Rock The Ridge is a 50-mile endurance challenge set in the scenic Shawangunk Mountains of the Mohonk Preserve. The event also features a trail marathon and relay options, all while raising funds to support the preserve's conservation and ed..