Trail Running calendar near Simsbury 2026-2027

A flat, non technical trail 5K at Schodack Island State Park on June 7, 2026, with kids races, post race music and a BBQ. Entry fees rise by registration period and kids races cost five dollars each.

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

A 5K trail and obstacle run on the 400 acre campus of Gaylord Specialty Healthcare in Wallingford CT, featuring 24 obstacles and a festival area with vendors, live music, and food trucks, supporting the Gaylord Sports Association.

Experience a scenic evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

Six hours of looped trail running at Ansonia Nature Center on Saturday June 13, 2026. The course uses roughly 1.9 mile singletrack laps with about 170 feet of elevation gain per lap and is limited to 69 runners.

Trail races of 50k, 30k and 10k through western Massachusetts hill towns on single track and dirt roads, held in partnership with Franklin Land Trust and featuring aid stations, first aid and locally produced awards.

A Last Human Standing trail race near Big River Management Area in West Greenwich, RI. Runners repeat the same loop each hour and must complete each lap within 60 minutes to remain in the field until only one athlete remains.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13 featuring mixed single-track and carriage-road terrain, water stations, finish-line food and music, and proceeds supporting local conservation.

A community event at Camp Edey on June 13, 2026 featuring a 5K run/walk and a 1 mile family walk, Family Day activities, race amenities, and age-group awards to benefit Girl Scouts of Suffolk County.

Trail races at Mansfield Hollow State Park: a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K trail loop. Proceeds support Connecticut trail stewardship groups.

A community 5K trail run, walk, and hike at Eisenhower Park in Milford on June 14, 2026, on a high school cross country course. The event supports the Milford Rotary and Beth El Center and includes music, water, snacks, awards, and T shirts..

A 53 mile ultramarathon across the Catskills with 15,000 feet of elevation, technical terrain, nine aid stations and a 23 hour limit. The course runs from Windham to downtown Phoenicia and emphasizes self sufficiency without pacers.

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

A loop trail run at Lawson Lake Park on June 20, 2026, featuring a 1.25 mile course with lake and creek views. Options include 2.5M, 5M, a one-hour format, and team entries; awards and a meal ticket are included.

An 8.6 mile trail run at Minnewaska State Park Preserve on June 24 with chip timing and commemorative towels for finishers. Entry is limited to 250 runners and parking carries a 10 USD per car fee.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

Test your endurance at Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.

A 12-hour timed loop event in Hamden, CT on a 4.25 mile course with 500 feet of gain per loop. Options include marathon, 50K, and 50 mile attempts, with proceeds supporting the Brooksvale Gift Fund.