Trail Running calendar near East Hampton 2026-2027

Trail races at Mansfield Hollow State Park with a 15-mile out-and-back on the Nipmuck Trail and a new 5K route; proceeds support Connecticut trail stewardship and the event is organized by Shenipsit Striders.

A community 5K trail run, walk, and hike at Eisenhower Park in Milford on June 14, 2026, on a high school cross country course. The event supports the Milford Rotary and Beth El Center and includes music, water, snacks, awards, and T shirts..

A family-friendly three-loop course of about 5 km through Natick Community Organic Farm with mixed trail, field and road surfaces. All participants receive a chicken medal and proceeds support the farm’s education and teen programs.

A morning trail run at Gay City State Park on June 20, 2026, offering 8 mile, 5 mile and 3 mile races. The 8 mile joins regional trail series and includes team competition with prize money.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

TSR Trail Race is a loop-format trail run on June 21, 2026, in Adams, MA, featuring hand and machine built singletrack with climbs, descents, and a gravel meadow loop; proceeds support Thunderbolt Ski Runners' trail stewardship.

Three summer trail races at West Hill Dam in Uxbridge, MA, with well-marked wooded single and double-track courses, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

Test your endurance at Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.

A 12 hour looped endurance event at Brooksvale Park in Hamden CT. Runners complete 3.1 mile loops with about 300 feet of gain and aid at each loop, with proceeds supporting local trail maintenance.

A Spartan obstacle weekend at Carter and Stevens Farm in Barre Massachusetts featuring a 5 km Sprint, a 10 km Super, kids races, and an obstacle workshop across mud, woods, and rolling hills.

A 3.1 miles moonlight trail run at Lakeside Park in Pawling, NY with varied terrain, glow markers, required personal light, post run towel and a handmade finisher medal. Proceeds support the Pawling Recreation Department.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.

A 5 mile loop run at the Cumberland Monastery with options to turn back early or add miles after the loop. The meeting point is behind the senior center where two trails join at the dirt parking lot and parking is ample.

A trail event at Red Wing Recreation Area on July 5, 2026, offering 15K, 30K, and 60K options across a 15k loop with mixed terrain, on-course aid stations, post-race food, and awards for top finishers.

A five-race Monday evening cross country series at Wickham Park in Manchester CT, the 35th edition features roughly 2.4 to 2.6 mile courses, a discounted full-series entry, and proceeds supporting the Manchester High School Shoe Fund.

Notchview Ultra is a multi day running event July 10-13, 2026 in Windsor, MA featuring fixed distance and timed races on a 1.9 mile loop with an aid station, camping logistics, and charity fundraising.

A point to point 5K in East Hampton beginning at the Connecticut Draft Horse Rescue with shuttle transport from Center School. Bib pick-up is at Center School gym and awards are presented by age group after the race.

New for 2026 at Putnam Memorial State Park, The Revolution is a timed trail event run on a 1.776 mile loop that passes Revolutionary War sites. Runners choose 12 hour, 6 hour, or 3 hour formats and carry their own hydration.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.