Trail Running calendar near Waterford 2026-2027

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.

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..

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.

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.

A 5.5 mile trail race at Soapstone Mountain with six steep ascents, a cupless water stop, strict parking limits and online registration capped at 50 runners; the course is technical and not recommended for novices.

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.

The Muddy Dash - Boston will take place in Charlton on Saturday 1 August 2026.

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.

A seaside set of timed ultra-marathon events at Colt State Park in Bristol, Rhode Island, offering 6 hour, 12 hour, and 24 hour formats with separate entry periods and fees.

A trail event at Noon Hill Reservation in Medfield offering a 10 mile loop plus 50K and 40 mile ultra options, mostly singletrack with roots, rocks, and a scenic Noon Hill vista; proceeds benefit The Trustees of Reservations.

A 2.5 mile trail run at Wildwood State Park on August 8, 2026. The rain or shine event offers live results and free finish line photos and benefits the Friends of Wildwood State Park.