Trail Running calendar near Cumberland 2026-2027

Join a friendly, informal 5 to 10k run or snowshoe on a roughly 10k course with loaner snowshoes available. Bring a spare pair to share, enjoy light refreshments, and team up for bragging rights and a shared baked treat.

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 the Frozen Heart 900, a free grassroots winter loop in Rockfall CT where runners take on a 15 hour challenge around a 2.2 mile trail loop. Self supported format with a heated meeting room for warming, so bring headlamps and carpool.

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 scenic singletrack loops around ponds and woodlands at Hale Education in Westwood, with a 6 hour endurance option or a 3.5 mile loop. Bring your own bottle for this cupless event and enjoy a laid back aid station at the start.

Tackle roughly 16 miles on the scenic, technical Nipmuck Trail in Union, Connecticut, running an out and back through Yale Myers Forest to Boston Hollow. Field capped at 100 with limited aid and no race day registration; proceeds support lo..

CT123 is a point to point 123 mile ultramarathon across Connecticut, blending trails and backroads for a scenic, challenging adventure. Choose solo 200K or 100K or team relay options, and earn a buckle or medal plus a 2025 race tee.

Join the Tortoise and the Hare Trail Races in Salisbury on April 4, 2026 for trail 10K, 5K and a fun 1 Mile Color Run. Enjoy custom tech shirts, post race music and snacks while supporting Salisbury Parks and Recreation.

Join the Merrimack River 10 miles on April 11 for a USATF sanctioned out and back trail race starting behind the DoubleTree in Andover. Enjoy water stops, post race bagels and a raffle while supporting local trail maintenance.

Explore wooded trails at Wompatuck State Park in Hingham with 5K, 5 mile and 8 Hour options on April 11. Expect mud, climbs, aid stations and community snacks plus custom finisher awards and bonus swag for early registrants.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Take on the Traprock 50 at Penwood State Park in Bloomfield, CT on April 18, 2026. Choose a rugged 50K of three rolling, rocky loops or a single 17K loop along technical single track and scenic forest roads. Bring your own cup.

Enjoy smooth loop trails in Jericho Town Forest with distances from 10K to 50K and a free youth run. This cupless race often sells out so register early and bring your own hydration for vegan friendly aid.

Tackle the rugged Seven Sisters Trail Race on May 2, 2026 along the Holyoke Range ridgecrest in Amherst, MA. This 12 mile out and back packs over 3,500 ft of climbing on technical singletrack with steep, rocky ledges for a true trail challe..

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

Take on scenic singletrack at the Mount Archer Trail Race in Lyme CT on May 3, 2026 with a tough 9.2 mile loop or a fun 3 mile sprint. Chip timed results, post race food and drinks, and proceeds support the Lyme Fire Department and Lyme Amb..

Hit the trails at the Cape Cod Trail Race on May 3, 2026, with 10K, 20K and 30K options through the scenic Frances A. Crane Wildlife Management Area. Register soon for a community focused day of challenging trails and postrace camaraderie.

TARC Wapack and Back in Ashburnham MA features 21.5, 43 and 50 mile out and back runs on the classic Wapack Trail. Rugged rocky singletrack, big climbs and sweeping views, plus aid stations and headlamp requirements for longer distances.

Explore Soapstone Mountain trails in Stafford Springs with a new half marathon that climbs past the fire tower or a fun 6K sampler open to walkers. Proceeds benefit Connecticut trail stewardship. The event is cupless so bring your own water..

Hit the trails at the Wildcat 5K Trail Run Walk Wag in Boxford on May 30, 2026, for a scenic 5K through Wildcat State Forest with pond views and separate courses for runners and walkers. Enjoy post race treats, swag, and prizes for top fini..