Trail Running calendar near Westerly 2026-2027

Watuppa Trail Races on May 9, 2026 in Fall River MA offers scenic, runnable trail courses through the Watuppa Reservation with fast grassy fire lanes and winding single track. Distances include 10K, 30K, and 50K.

A new Soapstone Mountain Half Marathon debuts in 2026 alongside the Jerry Stage 6K. Both are trail races in Shenipsit Forest starting at Reddington Rock Riding Club, organized by the Shenipsit Striders with proceeds to trail stewardship gro..

A *3.5 mile* trail run/walk at Woodtick Recreation Area in Wolcott, CT on May 17, 2026. Proceeds support the Wolcott Cross Country Teams and participants receive a free entry to the CT Food Truck Battles Festival.

The 4K Trail Run will take place in Boston from Wednesday 20 May 2026 to Thursday 21 May 2026.

A road half marathon in Roxbury, Connecticut on May 24, 2026 that features mixed pavement and dirt sections, notable climbs including a 250 foot gain near the halfway point, and a post race celebration at Mine Hill Distillery.

Trail races at Powisset Farm in Dover MA run through farm fields and Noanet Woodlands with four distances from 1.5 to 8.3 miles. One aid station provides water and this is a cupless race so runners must bring their own hydration carrier.

A point-to-point ultramarathon on the New England Trail offering 112-mile and 50-mile options to Guilford. Entrants must make a donation to the Connecticut Forest and Parks Association and arrange their own crew and navigation.

Run a scenic 3 mile trail through farm fields and finish among the vineyard rows at Westport Rivers Vineyard and Winery. Celebrate after with wine, music, BBQ and a souvenir glass for a festive postrun party.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

The Norbrook Farm Brewery Trail Festival will take place in Colebrook on Saturday 13 June 2026. You can run between 5 and 4 hours.

A six hour trail run at Ansonia Nature Center on June 13, 2026, run as counterclockwise loops of about 1.9 miles on moderately technical singletrack with roughly 170 feet of gain per loop. Entry is limited to 69 runners.

A trail running event at Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new 5K course entirely inside the park. Proceeds support Connecticut trail stewardship groups.

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

Twelve hour timed run on a 4.25 mile loop with about 500 feet of gain per loop in Hamden, CT. Options include marathon via six loops, 50K via eight loops, and a 50 mile target; proceeds support the Brooksvale Gift Fund.

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

A 5.5 mile trail race at Soapstone Mountain featuring six ascents and about 1500 feet of climbing. The route circles the mountain with multiple steep rocky sections, limited aid access, and a field limited to 50 runners due to parking.

Run the Stonington Cross Country 5K in Pawcatuck at Stonington High School on Wednesday August 5. The scenic course starts and finishes on the track and winds through quiet streets, trails and grassy crossings for a community run.

Experience the Trail Animals Running Club Summer Classic at Medfield's Noon Hill and Shattuck Reservations, a scenic and challenging 10 mile loop of forested singletrack that climbs to a Noon Hill vista. Distances include 10 miles, 40 miles..

Run loops on a roughly 5K trail course during an eight hour celebration with the Shenipsit Striders in Tolland. Bring food, enjoy the grill, earn raffle tickets and a 50th anniversary gift while supporting local trail stewardship.

Run the Old Goat Track Club XC Classic at Waters Farm in Sutton, a spike friendly 5K cross country loop and USATF New England Grand Prix stop. Perfect for teams and individual racers, with finish line snacks and a nearby after party.