Trail Running calendar near Old Lyme 2026-2027

A women only trail running event at Lake Mohegan in Fairfield, Connecticut on April 25, 2026, organized by Steep Endurance to raise awareness of trail running for women. Entry fees are listed between $30 and $80.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

Experience a scenic 5k trail run through conservation land and working farmland in Wrentham. Celebrate Earth Day with an off road course featuring natural obstacles and community focused agriculture support.

A student run community event on April 25, 2026 at MacDuffie School in Granby, MA featuring a flat cross country 5K and an optional Color Run, with 100% of proceeds going to Dakin Humane Society.

A spring trail race in Cross River, NY on April 26, 2026 offering a 10K course with entry by lottery. The $56 registration fee includes park entry and the race is USATF sanctioned; dogs are not allowed to run in the event.

Try the Trail is a youth trail run for ages 4 to 16 at Katonah Memorial Park. Kids can choose between a half-mile or one-mile course on scenic, easy-to-follow trails. It's a family-friendly event focused on outdoor activity.

Experience a technical 5 mile trail run through 250 acres of scenic green space in Killingworth. Navigate rocky terrain and elevation shifts at the Deer Lake Outdoor Center with awards for multiple age categories.

A 12 mile technical out and back trail race on the Holyoke Range near Amherst, MA, with more than 3,500 ft of elevation gain. Rocky singletrack ridgelines, two manned water stations, and registration currently shows full with a waitlist.

Celebrate National Truffle Day with a chocolate themed trail run at Giddings Park. This event features a three loop 5K for all ages and a kids fun run to support Franklin Elementary School programs.

A technical out and back 50K on New Haven blue trails with about 6,350 feet of climbing, strict time cutoffs, no crews or pacers, and multiple aid stations including water only stops.

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

Trail races in Lyme, Connecticut offering a 9.2 mile loop and a 3 mile sprint on Mount Archer trails. Chip timed and rain or shine, with 100% of proceeds donated to local emergency services.

Trail races at Watuppa Reservation in Fall River on May 9, 2026, featuring grassy fire lanes, winding single track and aid stations each lap. Distances offered are 10K, 30K and 50K.

A spring 10K trail race on Block Island that mixes dirt roads, coastal tracks, rolling pastures and a steep double tiered climb near mile four. Packet pickup and registration take place at the Block Island School.

Experience the eighth annual Spring Fling 600 trail races at YMCA Camp Sloper. Choose between a 6 mile race or a 10 hour challenge to complete as many loops as possible on a scenic three mile course.

A dog friendly 5K and a 2.6 mile walk at Borderland State Park on May 9, 2026 to benefit School on Wheels of Massachusetts. The event features refreshments, pup cups, kids pupsicles and free t shirts for early registrants.

A community event on May 9, 2026 featuring a Family Color Run and a 5K Trail Run at Hamden and New Haven YMCA locations. Registration runs from Feb 20 to May 8 with entry fees of $10 and $30; first 100 pre-registrants receive a Y giveaway.

Test your endurance on a 2.2 mile loop through the scenic Roosevelt Forest. This nine hour ultra event offers a supportive atmosphere for runners aiming to hit personal distance goals on classic New England trails.

A last person standing loop race on Ragged Mountain where runners repeat a roughly 3.11 mile loop and must finish each lap within one hour; entrants are eliminated if they fail to start or finish a lap, continuing until a single finisher re..

Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.