Trail Running calendar near Westport 2026-2027

A classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

Ascend twenty two floors at the Omni Providence Hotel during 이 premier indoor stair climbing event. Participants can join the open or firefighter categories to tackle three hundred and forty eight steps at their own pace.

Experience a USATF sanctioned 10 mile out and back trail run along the Merrimack River. Enjoy a community atmosphere with unique homemade prizes and support local trail maintenance efforts in Andover.

Experience an obstacle course race in Cumberland featuring a 3.2 mile loop with 1000 feet of elevation. Choose from competitive waves, multilap options, or a signature 12 hour ultra endurance challenge.

Shake off winter at the Spring Fever trail run in Wompatuck State Park. Choose from a 5K, 5M, or 8-hour ultra on a reversed course. All finishers get a custom award and can enjoy on-course support.

Test your endurance on a scenic five kilometer trail loop in Wrentham Massachusetts. This supported race offers forty and fifty mile challenges with a twelve hour cutoff and consistent access to aid stations.

A trail race at Jericho Town Forest (Weston, MA) on April 25, 2026 offering 10K, half, marathon, and 50K options on a marked 10K loop, cupless aid station, strict cutoffs, and parking by volunteers.

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.

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.

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.

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.

Experience an all trail race through the scenic Frances A. Crane Wildlife Management Area. Choose between 10K, 20K, or 30K distances on a repeating loop course in East Falmouth.

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.

Experience the varied landscapes of Block Island with a 10K course featuring coastal tracks and rolling pastures. Running through diverse terrain this spring event includes a steep double tiered climb and views of the Atlantic.

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.

Celebrate the eighth annual Trillium Spring 5K in Canton or participate virtually from anywhere. Join over 500 runners at the brewery to support Girls on the Run Greater Boston with races for adults and children.

Two trail races, a new half marathon and a 6k sampler, weave through the scenic Shenipsit State Forest past the Soapstone Mountain tower. The event supports local trail stewardship. A cupless race, it's organized by the nonprofit Shenipsit..

Join this adventure based event in Barrington featuring a 1.5 mile neighborhood loop and an accessible adaptive course. This family focused run includes electronic timing and performance shirts for the first 1,000 participants.