Trail Running calendar near Stonington 2026-2027

A trail race at Sleeping Giant State Park featuring more than 30 miles of varied terrain from carriage roads to technical rocky singletrack, presented as one of the tougher events in the Northeast and organized by Steep Endurance.

Run the perimeter of Heckscher State Park on smooth trails. Choose a 7-mile or 14-mile loop for a cupless, manually timed race. All finishers get a wooden medallion and a bucket hat.

A 123-mile point-to-point ultramarathon across Connecticut with a 36-hour limit, a mix of trails and roads, multiple mid-course cutoffs, and solo and relay options; finishers receive a buckle, medal, and event t-shirt.

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 an authentic off road adventure in Guilford with a 10k trail loop featuring technical single track paths and rock scrambles through Westwoods to support local land conservation.

A weekly Northampton cross country series held April through August on an accurately measured 5 km course through fields and woods. Day of registration is required, with modest fees and a season pass option.

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.

Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.

Join this dog friendly 5K trail run at Blydenburgh County Park to support animal rescue. Enjoy a scenic multi surface course with refreshments and professional timing included for all participants.

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.

The 11th Annual F.O.R 5k Trail Race takes runners through the scenic McDonald Nature Preserve in Wilbraham. This family-friendly trail run supports the local parks' maintenance fund.

Shore2Shore is a point to point trail event on the Long Island Greenbelt Trail between Sunken Meadow and Heckscher State Park offering 50K and 25K distances with fully stocked aid stations and a required two hour trail work contribution.

Trail loops at Penwood State Park near Bloomfield CT, with a **50K** (three loops) and a **17K** (one loop) on mixed technical single track and double-track terrain; the 50K has a nine hour cutoff.

The Brookhaven Trail 15K and 4 Mile runs explore the varied paths of Brookhaven State Park. This cupless event is capped at 250 runners and includes awards, refreshments, and supports veterans and local food banks.

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.

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.

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 out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.