Trail Running calendar near West Hartford 2026-2027

A community 5K trail run at Blydenburgh County Park on May 23, 2026, with in-person and virtual options, a free Kiddie Dash, on-site hydration and refreshments, parking guidance, and proceeds supporting the Never Stop Running Foundation.

A road half marathon in Roxbury, Connecticut on May 24, 2026 that features mixed pavement and dirt sections, notable climbs including a 250 foot gain near the halfway point, and a post race celebration at Mine Hill Distillery.

The IronHike Spring Endurance Series is a multi day mountain challenge in Connecticut. Choose from six timed events, from a 12 hour hike to an 84 hour ultra, all with massive elevation gain. Participants can go solo or team up in the unique..

A point-to-point ultramarathon on the New England Trail offering 112-mile and 50-mile options to Guilford. Entrants must make a donation to the Connecticut Forest and Parks Association and arrange their own crew and navigation.

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

The Rockwood Ramble 10K offers a scenic run on carriage roads through the woods of Rockefeller State Park Preserve. The event features a standard 10K and a separate kids' run, with all proceeds supporting trail maintenance.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

A six hour trail run at Ansonia Nature Center on June 13, 2026, run as counterclockwise loops of about 1.9 miles on moderately technical singletrack with roughly 170 feet of gain per loop. Entry is limited to 69 runners.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

A trail running event at Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new 5K course entirely inside the park. Proceeds support Connecticut trail stewardship groups.

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

Twelve hour timed run on a 4.25 mile loop with about 500 feet of gain per loop in Hamden, CT. Options include marathon via six loops, 50K via eight loops, and a 50 mile target; proceeds support the Brooksvale Gift Fund.

Trail racing at Red Wing Recreation Area with 15K, 30K, and 60K options on a 15k loop featuring varied terrain, aid stations, lap support for 60K runners, and post race food and drinks.

Notchview Ultra in Windsor MA runs multiple timed events on a 1.9 mile loop with an on-course aid station, campsite options, and beneficiaries including the Trustees of Reservations and Baypath Humane Society.

The Revolution is a new trail run on a historic 1.776-mile loop at Putnam Memorial State Park in Connecticut. Choose from 12, 6, or 3-hour timed events to test your endurance on gentle carriage roads. Part of your registration supports the..

A unique trail race at Soapstone Mountain featuring six ascents. Runners circle the base and climb each upward trail they find, finishing with the infamous Killer Hill. The challenging course includes rocky and steep terrain.

Discover a new trail running challenge north of NYC at the historic Ward Pound Ridge Reservation. Choose from 25K, 50K, or 50 mile distances on a runnable course through scenic wooded trails. Enjoy post race refreshments and earn a unique f..

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

An 8 hour timed track event at Clapp Park on a certified 0.355 mile dirt and cinder loop, featuring chip timing, trackside bottle drop aid, age division awards, a possible virtual option, and proceeds benefitting the AYJ Fund.