Trail Running calendar near Waterford 2026-2027

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.

The Ospreys Dominion Wine Run 5K will take place in Northville on Saturday 20 March 2027. You can run 5 kilometers.

A trail 5K and free kiddie run at Bethpage State Park with soft trails, event shirts, post race refreshments and a virtual option; proceeds support the Never Stop Running Foundation.

A spring trail out-and-back on the Nipmuck Trail near Bigelow Hollow, advertised as 16 miles on technical, blazed singletrack with minimal aid and limited parking; proceeds support local trail stewardship.

A point to point 123 mile ultramarathon across Connecticut from East Thompson to Southport with trail and road sections, a 36 hour cutoff, relay options, and staffed aid stations.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk in Blydenburgh County Park, Smithtown, NY held in April. The course uses mixed trail surfaces, offers on-site refreshments and hydration, supports Last Chance Animal Rescue, and includes dog-friendly park rules.

An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.

The Traprock 50 will take place in Simsbury on Saturday 17 April 2027. You can run between 17 and 50 kilometers.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A 12-hour looped hill event on May 22, 2027 in Cumberland, RI where participants run or hike as many laps as possible; the top male and female by distance are named King and Queen of the Hill.

A 5K trail run/walk at Blydenburgh County Park with mixed terrain, parking options, on-site refreshments and a virtual participation choice. Proceeds support the Never Stop Running Foundation.

The inaugural F.I.T. 50k in Cumberland, Rhode Island is a 50k trail ultramarathon with equal parts smooth non technical and moderately technical terrain. The event includes a generous cutoff time and a $65 registration fee.