Trail Running calendar near Holliston 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 trail running event in Rollinsford, New Hampshire featuring a *5 Miler*, a *5K*, and a Canicross 5K with rail trail and single-track sections along the Salmon Falls River.

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

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..

Run a unique 4 km trail race on Cathleen Stone Island in Boston Harbor. The event includes a ferry ride to the island and concludes with a post-run party. Proceeds support free science education for Boston youth.

A lap-based trail race in Keene NH using a 12.5 km loop with options up to 50 km, technical wooded terrain, aid stations, and a cupless policy requiring personal hydration gear.

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.

The Wildcat 5K Trail Run-Walk-Wag is a trail event on May 30, 2026, featuring separate courses for runners and walkers around Wildcat State Forest. Starting at Danvers YMCA Camp overlooking Stiles Pond, the event offers prizes, treats, and..

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 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.

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

Run a scenic 3-mile trail through vineyards and farms at Westport Rivers Winery. After the race, enjoy a dinner with wine and live music. All runners receive a souvenir wine glass.

A trail event in Dunstable MA featuring a marked 5-mile loop with about 600 feet of elevation per loop and a 6-hour option to run multiple laps; proceeds benefit the Humane Society for Greater Nashua.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

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.

A 13.1-mile trail race in Lynn Woods Reservation on June 21, 2026, run as three 4.4-mile loops over singletrack, carriage roads and fire roads, with a focus on sustainability, safety and community engagement.

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.