Trail Running calendar near Stafford 2026-2027

Tackle the TARCtic Frozen Yeti at Hale Education in Westwood MA on Feb 7 and 8 2026 with a 30 hour challenge or a 15 mile looped race. Expect well marked winter trails, regular aid and proceeds supporting land conservation.

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.

Run scenic singletrack loops around ponds and woodlands at Hale Education in Westwood, with a 6 hour endurance option or a 3.5 mile loop. Bring your own bottle for this cupless event and enjoy a laid back aid station at the start.

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.

Trail running at Sleeping Giant State Park in Hamden CT with 25K and 50K loop options, steep rock scrambles, aid stations, and a summit at the Observation Tower.

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.

Join the Merrimack River 10 miles on April 11 for a USATF sanctioned out and back trail race starting behind the DoubleTree in Andover. Enjoy water stops, post race bagels and a raffle while supporting local trail maintenance.

Trail running at Wompatuck State Park offering 5K, 5M, and an 8 hour lap option limited to 50 runners. Staggered starts, aid stations, drop bags, no dogs, and registration closes April 10.

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.

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.

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 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.

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.

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..

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

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

Take on scenic singletrack at the Mount Archer Trail Race in Lyme CT on May 3, 2026 with a tough 9.2 mile loop or a fun 3 mile sprint. Chip timed results, post race food and drinks, and proceeds support the Lyme Fire Department and Lyme Amb..