Trail Running calendar near Hamden 2026-2027

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..

A chip timed 5K at Osprey's Dominion Vineyards in Peconic, NY on March 20, 2027. Entry includes a t-shirt, collapsible wine glass, finisher medal, chip timed bib and a pour of wine.

The Enchanted Forest Ultra Run will take place in Stratford on Saturday 20 March 2027.

A 5K trail run at Bethpage State Park with a free kiddie fun run and a virtual option, a good luck shirt, on course hydration, post race refreshments, and age group recognition. Beer is available for participants 21 and older with ID.

On March 28, 2027 this roughly 16 mile out and back follows the Nipmuck Trail through Yale Myers Forest and Bigelow Hollow State Park. Registration opens Jan 1, 2027, parking is limited and a waitlist is used.

A 5K trail run and a free kiddie run at Bethpage State Park with in-person and virtual options, onsite refreshments, mailed bibs, and online results. Donations support the Never Stop Running Foundation.

A point-to-point ultramarathon across Connecticut, Run Across CT 123 covers about 123 miles from East Thompson to Southport with trail and road sections, a 36-hour cutoff, solo and relay options, volunteer-supported aid stations, and finish..

A mountain trail event at Harriman State Park offering a half marathon, a 10K, and a 10K ruck on rugged, technical courses with significant elevation gain and limited crew access at aid stations.