Trail Running calendar near West Greenwich 2026-2027

Run a point to point ultramarathon on the Midstate Trail across Massachusetts with crossings into NH, RI and CT. Choose 100 Mile, 50 Mile or 50K routes through woodlands, fields and rivers at peak fall.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Enjoy a scenic 3 mile trail at Sakonnet Vineyard, then celebrate with wine, dinner, music and a souvenir wine glass. BBQ only and kids BBQ options are available for those who prefer to skip the run.

Join a scenic trail run through NE Connecticut along the Air Line State Park Trail with marathon, half, 10K, relay and junior distances. Tackle the Trail supports local students pursuing higher education.

Run the Ghost Train Trail in Brookline, New Hampshire amid peak fall foliage. Choose ultramarathon, relays, haunted 30 mile night or 15 mile race and help fund local conservation and trail preservation.

Join the Womp Romp at Wompatuck State Park for muddy, scenic trail loops through South Field with 10 Miler and 50K options and hearty aid stations. Proceeds support local charities for a fun, community focused fall run.

Discover scenic single track trails at Grills Preserve in Westerly on October 24, 2026 with 10 mile and 10K options. Choose a distance and enjoy riverfront views and bridges as race two of the WTAC Fall Trail Race Series.

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.

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.

TARC Winter Classic offers 8 32 and 40 mile trail races on the rugged Middlesex Fells Skyline Trail with roots, rocky climbs and occasional Boston skyline views. Affordable entry and proceeds support land conservation.