Trail Running calendar near Chester 2026-2027

A free community trail event in Farmington offering shoe demos and short runs on local trails. Options include about 5 km, 1.7 mile, and 1 mile routes, with snacks and drinks afterwards.

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

A 5K trail and obstacle run on the 400 acre campus of Gaylord Specialty Healthcare in Wallingford CT, featuring 24 obstacles and a festival area with vendors, live music, and food trucks, supporting the Gaylord Sports Association.

Experience a scenic evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

A six hour looped trail run at Ansonia Nature Center on roughly 1.9 mile counterclockwise singletrack loops with about 170 feet of gain per loop. Field capped at 69 runners; no crews or pacers; early signup includes a shirt and swag.

A low key trail event in Ashfield, MA on June 13, 2026 that showcases local trails and preserved lands. It offers 50 km, 30 km and 10 km distances and raises funds for the Franklin Land Trust.

A loop based endurance race near Big River Management Area in West Greenwich, RI where runners must complete each circuit within 60 minutes to continue; laps repeat at one hour intervals until only one runner remains.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13, 2026, with routes on single track trails and carriage roads. Proceeds support Mass Audubon conservation; water stations, finish area refreshments, and limited parking.

A community 5K and untimed 1-mile family walk at Camp Edey in Bayport supporting Girl Scouts of Suffolk County. The day includes family activities, finisher medals, event shirts, and awards while raising funds for scholarships and programs.

A mixed-surface 5 km race and one-mile fun run at Hampshire Regional High School in Westhampton on June 13, 2026. The 5 km combines paved roads and wooded trails; awards, refreshments, restrooms and parking are provided.

Trail races in Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new in-park 5K, with varied terrain, marked courses, and proceeds benefiting 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.

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.

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 timed loop event at Brooksvale Park in Hamden, CT on June 27, 2026, using a 4.25 mile loop with 500 feet gain per loop. Options include marathon and 50k loop targets, aid at each loop, and proceeds aid 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 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.