Trail Running calendar near Stoneham 2025-2026

Run a scenic 5 mile route along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot while supporting the Fitzwilliam and Troy Historical Societies. Food, festivities and a short kids loop make it a great community day.

Run a scenic 3 mile trail through farmland and finish among the vineyard vines at Westport Rivers Winery, then enjoy wine, BBQ, live music and a souvenir glass. Race entry is 21 and over while BBQ options welcome families.

Run the rugged Flat Rock Trail Race in Dunstable MA on June 13, 2026. Choose a single 5 mile loop or take on a 6 hour loop challenge across rocky climbs, old railroad bed and an arched bridge while supporting the Humane Society for Greater..

Run the scenic 15.7 mile Nipmuck South Trail at Mansfield Hollow State Park, following the Nipmuck Trail along the Fenton River through woods, fields and a climb to a cliff. Proceeds benefit Connecticut trail stewardship groups and the Blue..

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..

The Soapstone Assault is a rugged 5.5 mile trail race in Somers, CT with six climbs and about 1,500 feet of ascent. Limited to 50 runners, it is a tough course for experienced runners and includes a pre race safety briefing and breakfast.

The Shenipsit Striders Fatass will take place in Tolland on Saturday 15 August 2026. You can run 5 kilometers.

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.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

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 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.

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.