Trail Running calendar near Simsbury 2026-2027

Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.

Trail 10K in Bloomfield CT on Nov 1, 2026 honoring Kevin Hutt, run on rocky single track in Penwood State Park with proceeds partly to NAMI.

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.

Looped trail event at White Barn Farm on Nov 7, 2026, where runners complete 3.1 mile loops and choose how far to go.

A trail event at Ward Pound Ridge Reservation featuring a 10 km race, a November 100 km virtual challenge, rugged climbs, and fundraising for the Friends of Trailside Museum.

A 5k chip-timed run/walk at Stonington Vineyards on November 8, 2026 featuring a two-lap cross country route through the vines. Registration includes a shirt, collapsible wine glass, finisher medal and a pour of wine.

Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.

A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.

Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

Trail races at YMCA Camp Sloper on November 21, 2026 offering a 400 minute loop event and a 4 mile race with chip timing and on-course aid.

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.

A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.