Trail Running calendar near Waterbury 2026-2027

A 10K trail race at Penwood State Park in Bloomfield, CT on November 1, 2026. The rolling loop follows mostly technical single track on the Metacomet, Orange and Yellow trails, has no on course aid station and a three hour cutoff.

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 trail event at Ward Pound Ridge Reservation combining a 10 kilometer trail race with a November virtual 100k challenge, volunteer support, postrace results, and a finisher woodallion for reported 100k totals.

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.

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 races at Tarrywile Park in Danbury, CT offering 10K, half marathon and marathon options on technical single track; the half uses a loop with close to 3K of elevation and a cupless race policy.

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.

A scored 5K cross country race at Van Cortlandt Park on November 15, 2026, part of the NYRR Cross Country series, with live app tracking, on-site awards, a member standby list, and youth programming for ages 2 to 18.

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 a roughly two-mile loop: a 400 minute time-limit event with loop counting and a four mile two-lap race, chip timing, a single aid station, cupless policy, and proceeds to local organizations.

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 community 5K run/walk through Inwood Hill Park with live results, free finish-line photos, awards for the top two men and women, and proceeds supporting the Inwood Food Pantry.

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.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

Looped 50-mile and 50k races in Prospect Park, Brooklyn on December 6, 2026, run on 3.33 mile laps starting and finishing near the Lincoln Road Entrance. Hydration is provided by Skratch Labs and a 15 hour cut-off applies.

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.

A winter trail event at Ramapo Valley County Reservation on February 14, 2027 featuring a flat, scenic lollipop loop around Scarlet Oak Pond. Participants are encouraged to wear onesies; the event includes an aid station, finishers medal, a..

Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and f..