Trail Running calendar near Andover 2025-2026

Explore rugged singletrack and an old railroad bed on a tough 5 mile loop at the Flat Rock Trail Race in Dunstable MA. Proceeds benefit the Humane Society for Greater Nashua and runners can repeat loops for up to six hours.

Test your trail skills at the Spaulding Woods 50K, a challenging multi lap race on rocky singletrack and scenic footbridges around Northfield, New Hampshire. Well supported and community focused, the event benefits Spaulding Academy & Famil..

Run the Ragged 75 multi day stage race or choose the single day 50k on rugged trails around Lake Sunapee, NH. Big climbs, scenic single track, communal camping and a true self supported trail challenge.

Hit the fields at Waters Farm on Sunday, August 23, 2026 for the Old Goat Track Club XC Classic, a fast and friendly 5K cross country through scenic farm trails. A USATF New England Grand Prix stop with race day registration available.

Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.

The Mt. A Trail Challenge will take place in York Harbor on Saturday 19 September 2026. You can run 5 kilometers.

Hit the newly restored Moosup Valley State Park Trail on Sunday, September 27 for scenic 5K, 10K and a kids fun run on all trail terrain. Post race food and gear, leashed dogs welcome, and proceeds support the Rotary Club of Plainfield.

Run scenic, rooty trails in Groton Town Forest on October 4 with 9.5 mile and 3.4 mile options through rolling hills and rocks. Limited to 250 runners with refreshments and awards.

Tackle the rugged NipMuck Trail Marathon in Ashford CT, a 26.4 mile trail test through rocks, roots, mud and wooden bridges. Run solo or as a two person relay and expect a challenging, hilly second half that rewards grit.

Tackle the Midstate Massive Ultra Trail, a UTMB Index point to point across New England following the historic Midstate Trail. Choose 100 mile, 50 mile or 50k routes through mountains, fields, roads and rivers for a multi state adventure.

Celebrate the 20th Wayland HFC Striders Cross Country Festival on October 11, 2026, a family friendly meet supporting Wayland High School programs. Youth 3K plus open 5K races, trophies and local sponsors make for a fun community day.

Enjoy a scenic 3 mile trail run at Sakonnet Vineyard in Little Compton on October 17, followed by wine, BBQ, live music and a souvenir wine glass. Adults 21 and up get timed racing, a race shirt and a festive post race party.

Womp Romp is a trail race at Wompatuck State Park with scenic single track, wider trails, and some paved sections. Choose a 10 mile one loop or a three loop 50K and enjoy friendly aid stations and a community vibe supporting local charities..

Experience rugged single and double track in Willowdale State Forest at the TARC Stone Cat Trail Festival in Ipswich, with distances from 10K to 100K and a Cider Donut Mile for fun. Proceeds support land stewardship and local food pantries.