Trail Running calendar near Somers 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 Trail Animals trail event at Hale Education in Westwood offering a timed six hour option and a 3.5 mile singleloop on mostly singletrack around ponds. One cupless aid station at start/finish and limited parking with possible walking.

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..

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 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.

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.

The The Blue 2 Blue Challenge will take place in Woodbridge on Sunday 3 May 2026. You can run 50 kilometers.

A trail event at The Hartsbrook School in Hadley featuring a 5K Dandelion Dash and a 1 mile Mushroom Mile. Proceeds support school land stewardship and a virtual 5K option is offered.

Trail races in Lyme, Connecticut offering a 9.2 mile loop and a 3 mile sprint on Mount Archer trails. Chip timed and rain or shine, with 100% of proceeds donated to local emergency services.