Trail Running calendar near Waterford 2026-2027

A multi distance trail event in Rocky Point, NY from October 9 to October 12, 2026, run on a 10.48 mile loop with two aid stations. Distances range from 10 mile to 150 mile and runners must complete the distance they start.

Trail races at Mohawk Mountain Ski Area in Cornwall CT offer 5K, 10K, half marathon and marathon courses across ski trails and Mohawk State Forest, with notable elevation gain, cupless aid policy, finisher medals and overall awards.

A trail run at Sakonnet Vineyard in Little Compton on October 17, 2026, covers about 3 miles of uneven trails and finishes among the vines. After the run there is dinner, wine, music and a souvenir wine glass for race participants.

A two day running event in Bay Shore, NY featuring marathon, half marathon, 10K, 5K, kids runs and a virtual challenge. Proceeds benefit local veterans and the event has raised over $1,000,000 to date.

Tackle the Trail on October 17, 2026 is a point to point trail race along the Air Line Trail State Park between Willimantic and Putnam. Distances include marathon, relay marathon, half marathon and 10K with four staffed relay stations.

The Tom Centinaro Memorial "Dam" Race will take place in Waterbury on Saturday 17 October 2026. You can run 4 miles.

The Grills Trail Run will take place in Westerly on Saturday 24 October 2026. You can run between 10 and 10 miles.

The Pumpkin Pacer 5k will take place in Wrentham on Saturday 24 October 2026. You can run 5 kilometers.

A 5 mile trail race at Muscoot Farm in Katonah with two kids races by age group, Farm Bucks for the farmer's market, optional shirts, and no dogs permitted except trained service dogs.

Rugged 5k trail run, ruck, or walk in Berkley MA on October 25, 2026 with in person and virtual options. Dogs may join on leash with a waiver and proceeds support The Baystate Beagle Club and Give2Those.org.

Timed trail event at Gurski Farm in Brookfield CT featuring continuous 4 mile loops for 8 hour and 4 hour runners plus new 5K and 5K Canicross options. Post race food and beverages are provided.

A trail 10k at Ward Pound Ridge Reservation paired with a November virtual 100k challenge that rewards finishers with a custom engraved woodallion; the race uses rocky ridgeline trails and includes an on-course water stop near the fire towe..

A technical trail event at Tarrywile Park in Danbury offering 10K, half marathon and marathon distances with significant elevation gain; finisher medals, podium awards, and post-race food are provided.

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.

A trail half marathon in Roosevelt Forest on November 21, 2026, run as eight 1.64 mile loops over singletrack and doubletrack with roots, rocks, and rolling hills. Costumes are encouraged and a book drive supports Books4Everyone.

Join the Soul n Body Thanksgiving Trail Run in Wolcott CT for a spirited 3.5 mile loop around Mill Pond Way, complete with finisher medals, swag and post race yoga. Proceeds benefit endometriosis research and furry friends are welcome.

A timed out and back event on the Tower Trail at Sleeping Giant State Park where runners repeat roughly 3.3 mile laps to the Observation Tower in four hour or eight hour formats. Aid is at the start and finish and the race follows a cupless..

A 5K trail race at Roosevelt Forest in Stratford, CT on December 19, 2026, run over two 1.55 mile loops. Holiday costumes are welcome, awards are given to top finishers, and all finishers receive a custom medallion; proceeds support local c..