Trail Running calendar near Sterling 2026-2027

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

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.

Hit the trails at the Wildcat 5K Trail Run Walk Wag in Boxford on May 30, 2026, for a scenic 5K through Wildcat State Forest with pond views and separate courses for runners and walkers. Enjoy post race treats, swag, and prizes for top fini..

A scenic 2.5 mile off-road run or walk around Horn Pond paired with a festival at Ice House Park featuring food trucks, a DJ, raffles, kids activities, and over 25 local mental health and substance use providers.

A multi day endurance series at Mohawk Mountain in Connecticut offering solo and team trail events from 15 to 152+ miles with timed formats up to 84 hours. Tenting, support stations, and personalized bibs and medals are provided.

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 5 mile Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on Saturday, June 6, 2026. Enjoy family fun, food, and festivities while supporting the Fitzwilliam and Troy historical societies.

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.

Challenge yourself on the Flat Rock Trail Race in Dunstable MA on June 13 2026 with a scenic 5 mile loop or a 6 hour looped event, featuring rolling climbs and single track trails. All proceeds benefit the Humane Society for Greater Nashua.

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.

Stone Tower Half Marathon is a 13.1 mile trail race in Lynn Woods Reservation run as three identical loops that pass the historic Stone Tower. The course features forested singletrack, rocky trails and carriage roads and emphasizes environm..