Trail Running calendar near Pawcatuck 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.

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 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 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.

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 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.

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 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.

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..

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.

A 1 mile out and back on the Farmington Canal Heritage Trail with a crushed gravel surface and hand timing. Held July 19, 2026 in East Granby in two waves with limited parking; proceeds benefit charities.