Westport
Trail Running Calendar near Westport 2026-2027
Explore the top trail runs near Westport for 2026-2027! We've gathered 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Second annual fall trail run and walk at Ryan Park in North Kingstown, RI; a 5K course with age group medals and proceeds benefiting the local firefighters association.
A park-based, traffic-free 5K in Highland Park, Attleboro with a grass loop course, a kids 100 yard fun run, on-site activities, awards, and a virtual 5K option.
A 5K and 1 Mile Fun Run at the Dighton Rehoboth High School cross country course raising funds for student Unified programs, with early registration and event awards.
A trail run through Sakonnet Vineyard on October 17, 2026 with an approximately 3 mile course and post-run wine, dinner and music.
A Fall River trailfest on October 17, 2026, with walks, runs, and a 10-mile ruck through the Bioreserve plus post-race music and family activities.
A rugged 5k trail run, ruck, and walk in Berkley MA on October 25, 2026 that honors military and first responder K9 teams while supporting local charities.
A 5K through the cranberry bogs at AD Makepeace in Wareham on October 31, 2026, with online registration open and awards for overall and age group finishers.
November 2026
A community 5K trail run at East Greenwich High School supporting local families and charities with proceeds to EG Unified Sports Program, Women & Infants NICU and Give Kids The World.
A 5K off-road run on the Mt Hope HS cross country course in Bristol with start and finish at Bristol Town Beach, with proceeds supporting Mt Hope HS indoor track.