Trail Running calendar near Simsbury 2026-2027

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..

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

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.

Test yourself on a challenging and scenic Connecticut half marathon. The course winds past farms and over historic bridges, finishing at a local distillery. Enjoy a post race celebration with food, drinks, and music.

This 5K cross-country run and walk takes place at Peach Hill Park in Poughkeepsie, reaching the town's highest point. It's open to all ages, with proceeds supporting the park's maintenance. Awards, snacks, and a rain date are part of the co..

Event Overview The IronHike Endurance Series - Spring is a multi-day trail endurance event taking place from June 4 to 7, 2026 at Mohawk Mountain Ski Area in Cornwall, Connecticut. It features a FlexRelay format where participants can tackl..

Overview The Connecticut Ultra Traverse (CUT) is a point-to-point trail running event with two distances. The CUT112 is a 112 mile run following the Blue Blazes of the New England Trail (NET) from the Massachusetts-Connecticut border to the..

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.

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..

Explore the trails of Mansfield Hollow State Park at the Nipmuck South Trail Race. Choose between a scenic 15 mile out and back route or a new, challenging 5K course. Proceeds support local trail stewardship organizations in Connecticut.

Manitou’s Revenge is a 53-mile ultramarathon through the remote Catskill Mountains. With 15,000 feet of climbing on rocky, steep trails, the course becomes progressively more difficult. It runs from Windham to Phoenicia on the Long Path.

Celebrate the longest day of the year with a trail run in Hebron, Connecticut. This event on June 20, 2026, features three distance options on the trails. Choose from a 3 mile, 5 mile, or 8 mile course.

Test your endurance on a 4.25-mile loop in Hamden, CT. Set a goal from a marathon to 50 miles within the 12-hour window. Your registration supports local trail maintenance and comes with unique swag.

The Red Wing Trail Challenge offers 60K, 30K, and 15K distances on a rugged 15K loop in Lagrangeville, NY. The course features mixed terrain and significant elevation gain on each lap. Post-race food and unique finisher awards are provided.

Notchview Ultra features a 1.9-mile groomed loop trail in Windsor, Massachusetts. The event includes multiple ultra distances from 6 to 72 hours and a 100.7-mile race. Proceeds support the Trustees of Reservations and a local 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.