Trail Running calendar near Little Compton 2026-2027

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.

A recurring, in-person group trail run for women and nonbinary people around the North Reservoir in Winchester, MA, covering a conversational 3 mile loop at about 11 to 12 minutes per mile. Sessions are led by local run leaders and cancel f..

A community running event on June 6, 2026 in Holliston with 5K, 10K, and a Kids Fun Run on the flat Holliston Rail Trail. Registration opens March 1; fees are $30 for the 5K and 10K and $5 for the kids run.

A 20 mile single-loop hike through Wompatuck State Park near Boston on June 6, 2026, with aid stations roughly every 5 to 7 miles, finisher medals and certificates. The event is currently sold out.

A group run on the Ocean State Ultra 10 mile loop in West Greenwich, RI. The route allows runners to turn back early and participants must wear orange because it is hunting season.

A trail run at Westport Rivers Vineyard & Winery on June 7, 2026, covering about 3 miles of mixed trails and finishing among the vines. The event includes dinner, wine, music and a souvenir wine glass, with BBQ only options available.

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.

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 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 trail half marathon in Lynn Woods Reservation on June 21, 2026, run as three identical loops over forested singletrack and carriage roads. The event emphasizes environmental stewardship and uses a centralized start and finish at the main..

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.

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 12 hour trail event in Lawrence Woods, Middlesex Fells Reservation near Medford MA on July 18, 2026. The course is a roughly 5 mile loop with a minimal aid station and parking at the nearby high school lot.

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.

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