Trail Running calendar near Vernon 2026-2027

A community 5K at Hampshire Regional High School combining paved roads and technical wooded trails, plus a one mile fun run around campus; post race refreshments and awards are provided.

Trail races at Mansfield Hollow State Park: a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K trail loop. Proceeds support Connecticut trail stewardship groups.

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 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.

Part of the Grit Series at Dublin Outdoor Center, this trail event offers a 10K and a half marathon over rugged trails with significant elevation gain and views of Mount Monadnock. Registration runs May 3 to June 6, 2026.

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.

A loop-format trail event in Adams, MA where runners choose one, two, or three loops on machine and hand-built singletrack. Proceeds support Thunderbolt Ski Runners' stewardship of trails around Greylock Glen and Mount Greylock.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, 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 timed loop event in Hamden, CT on a 4.25 mile course with 500 feet of gain per loop. Options include marathon, 50K, and 50 mile attempts, with proceeds supporting the Brooksvale Gift Fund.

A Spartan obstacle race weekend at Carter & Stevens Farm in Barre, MA, featuring a Sprint 5 km with 20 obstacles, a Super 10 km with 25 obstacles, and kids races. The farm venue includes mud, woods, rolling hills and a farm store.

A night 5K at Lakeside Park with mixed trail terrain, reflective markers, and required personal lighting; finishes receive handmade medals and proceeds benefit 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.

The Red Wing Trail Challenge in Lagrangeville, NY on July 5, 2026 offers 60K, 30K and 15K trail races with substantial elevation gain. The event includes aid stations, an interactive course map, on course fuel and post race food and drinks.

Notchview Ultra in Windsor, MA runs July 10-13, 2026 on a 1.9 mile loop with multiple time and distance options, an aid station, campsite planning, event SWAG, and proceeds benefiting local organizations.

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.

A 12K trail race on the Blue Hills Skyline Trail with about 2,300 feet of climbing, rocky steep terrain, and minimal aid. The route follows Skyline blazes from the Blue Hills Ski Area parking lot and requires participants to carry hydration..

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.