Trail Running calendar near Waterford 2026-2027

A winter trail event at Hale Education in Westwood offering a 30 hour ultrarun and a 15 mile looped course. The course uses three marked five mile loops, cupless aid stations, strict cold weather gear rules, and limited entry.

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

A 3 x 2 mile cross country relay at Sunken Meadow State Park in Kings Park, NY, marking the 47th running of the event. The program includes a youth division, a costume contest with prizes, post race refreshments and multiple age categories.

Looped hill races at Sunken Meadow State Park where the most distance in a three hour loop crowns the King and Queen, and a separate one hour event crowns the Prince and Princess.

Join the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park, a scenic trail run starting on a grassy polo field. Family friendly with a kiddie fun run, virtual 5K and post race refreshments supporting the foundation.

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

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.

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.

Join Last Chance's Run for the Rescue, a scenic 5K at Blydenburgh Park on April 11 with virtual entry through Apr 19. Bring leashed dogs, enjoy trails and refreshments, and support Last Chance Animal Rescue.

Community trail events at the John Jay campus in Cross River, NY featuring a 5k trail race, a 4k Jay Walk, and a 200 m Kids Jay Dash on the track. Woodland sections include hilly terrain and finishes are on the contest field.

A spring event at the Stamford Museum and Nature Center on April 12 2026 featuring a scenic 5K through farm and woodland and a 0.3 mile kids run past farm animals. Proceeds support the museum and nature center.

A point-to-point 50K and 25K on the Long Island Greenbelt Trail on April 18, 2026, featuring marked singletrack, five stocked aid stations, drop-bag options for 50K, and a two-hour trail-work requirement for entrants.

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 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.