Trail Running calendar near Southwick 2026-2027

The Frozen Heart 900 will take place in Rockfall on Saturday 7 February 2026. You can run 50 miles.

The Ospreys Dominion Wine Run 5K will take place in North Fork on Saturday 21 March 2026. You can run 5 kilometers.

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.

Run Sleeping Giant State Park on scenic, challenging trails with 25K and 50K options. Tackle runnable miles, rocky singletrack and a steep scramble to sweeping views, while supporting the park through registration proceeds.

CT123 is a point to point 123 mile ultramarathon across Connecticut, blending trails and backroads for a scenic, challenging adventure. Choose solo 200K or 100K or team relay options, and earn a buckle or medal plus a 2025 race tee.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

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..

Run or walk the John Jay Community Trail Race in Cross River through scenic wooded trails and rolling hills, with 5k, 4k walk and a Kids Jay Dash on the track. A family friendly community event that finishes on the John Jay Contest Field.

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.

Join the Brooklyn Cider House Spiked Apple 5K in New Paltz on April 19, 2026 for a chip timed run or walk. Enjoy a tee, cider pour, donut and a finisher medal that doubles as a bottle opener for a festive post race celebration.

The Brookhaven Trail 15K Run will take place in Wading River on Sunday 19 April 2026. You can run between 4 and 15 kilometers.

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 USATF-sanctioned ultramarathon around scenic Lake Waramaug in Kent, Connecticut on April 26, 2026, offering 100K, 50 mile and 50K options on paved, rolling loops with four aid stations and finisher awards.

A 10k trail race at Ward Pound Ridge Reservation in Cross River, NY on April 26, 2026. Entry is by lottery and registration includes park entry; the race is USATF sanctioned so dogs are not permitted to run.

Tackle the rugged Seven Sisters Trail Race on May 2, 2026 along the Holyoke Range ridgecrest in Amherst, MA. This 12 mile out and back packs over 3,500 ft of climbing on technical singletrack with steep, rocky ledges for a true trail challe..

Run to Remember on May 2, 2026 in Red Hook NY offers scenic 5K and 10K trail runs plus a 5K walk through meadows, orchards and forest. Honor loved ones and enjoy community spirit with cash prizes for top finishers.

A fundraising trail event in the Shawangunk Mountains on May 2, 2026 offering a 50 mile Ultra Marathon, a 26.2 mile Trail Marathon and two to four person relays. Proceeds support Mohonk Preserve conservation, education and stewardship.

A technical trail event near Beacon, NY on May 3, 2026 offering half and full courses with steep exposed climbs, significant elevation gain, aid stations, limited on-site camping, and a participant shirt and finisher item.