Trail Running calendar near Wading River 2026-2027

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..

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

The Jade's Belmont Plateau 5K will take place in New York on Saturday 20 June 2026. You can run 5 kilometers.

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 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.

Trail Night NJ is a Wednesday evening 5K on the trails at South Mountain Reservation in West Orange, NJ. The event also includes a short kids race and a central start and finish area with a DJ, vendors, food trucks, and a participant tee.

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.

Experience a unique four mile trail race through the historic Forest Park in Queens. Run along naturally carved glacial terrain and pine groves with your dog to support a local animal rescue organization.

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 one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

A timed trail event at South Mountain Reservation on July 25, 2026, where runners draw colored golf balls to determine each loop; charitable proceeds support Bigger Than The Trail and aid stations will provide Skratch Hydration.

A 5.5 mile trail race at Soapstone Mountain with six ascents and about 1500 feet of climb. The field is capped at 50 runners for parking reasons and online registration is required.

A trail running event at Ward Pound Ridge Reservation offering 25K, 50K and 50M courses across wooded singletrack and carriage roads with runnable sections, ridge views, aid stations, and GPX course files.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.