Trail Running calendar near Falmouth 2025-2026

Join the Mount Hood Nutcracker Challenge in Melrose for a festive 3.5 mile cross country race or 2 mile walk on the Mount Hood golf course. Enjoy nutcracker trophies, pasta lunch and fundraising for local families and Melrose High XC.

Tackle the TARCtic Frozen Yeti at Hale Education in Westwood MA on Feb 7 and 8 2026 with a 30 hour challenge or a 15 mile looped race. Expect well marked winter trails, regular aid and proceeds supporting land conservation.

Join Ramsey's Run in Kingston MA on March 14, 2026 for a scenic 5k trail run through the woods, timed by a professional company. Honor a class of 2023 member and support a family scholarship with every entry.

Run the scenic single track loop at Hale Reservation in Westwood, MA with 3.5 mile or 6 hour options. Trails, pond views and wood bridges await while proceeds support land conservation.

Run Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.

Hit the trails at Wompatuck State Park in Hingham MA with 5K, 5 mile and 8 hour lap options for all abilities. Expect muddy April trails, on course aid and a community feed, with registration closing April 10 and a 50 runner cap for the 8 h..

Run the TARC Spring Classic at Jericho Town Forest on April 26, 2025, choosing distances from 10K to 50K plus a free youth fun run. Enjoy a smooth, relatively flat looped trail with one aid station offering vegan friendly options.

The Cape Cod Trail Race will take place in Falmouth on Sunday 3 May 2026. You can run between 10 and 30 kilometers.

Experience the 9th annual Wildcat 5K Trail Run, Walk and Wag on May 30, 2026 in Boxford, a scenic 5K around Stiles Pond through Wildcat State Forest. Runners, walkers and their dogs will enjoy trails, prizes and a festive post race celebrat..

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.

Experience the Stonington Cross Country 5K at Stonington High School, a scenic route from the track through campus streets and wooded trails to a field finish. Family friendly with a kids half mile for ages 10 and under.

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.

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.

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.