Trail Running calendar near Andover 2026-2027

Run a scenic 50k on New England dirt roads. The course winds through forests and fields, featuring an 1870s covered bridge and 4,200 feet of elevation change. Registration closes a few days before the event.

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

Cross country 5K at Cole's Family Farm in Dayton on May 16, 2026 supporting the Southern Maine Young Marines. Options include a 1.25K fun run and a 5K ruck march; entry includes a patriotic t-shirt and participation medal.

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 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 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 two-lap mountain race at Mount Sunapee on June 7, 2026, serving as the USATF National Classic Mountain Championship and the Collegiate Mountain Running National Championships. About 9.2 miles and roughly 3,250 feet of elevation gain.

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.

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..

Spaulding Woods 50K is a trail ultramarathon in Northfield, NH on July 11, 2026. The race uses a technical 5.6 mile loop with rocks, roots and footbridges, requires six laps and a ten hour time limit, and supports Spaulding Academy.

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

The Kingman Farm Trail Race is an old-school, show up and race event over 3.8 miles of rolling nordic paths and switchback singletrack. It benefits the Doug Flutie, Jr. Foundation for Autism. Day-of registration is available.

A three day stage race around Lake Sunapee covering about 75 miles and 15,500 ft of climbing, with an optional 50k on the final day. The format includes overnight camping, gear transport, aid stations and strict gear requirements.

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

The 5K Race to the Ledges will take place in Concord on Saturday 8 August 2026. You can run 5 kilometers.