Westport
Trail Running Calendar near Westport 2026-2027
Explore the top trail runs near Westport for 2026-2027! We've gathered 9 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A family-friendly obstacle-course fundraiser on September 19, 2026 in Warren RI featuring a 1 mile course with large mud pits, food vendors, music, and activities for all ages.
A 5K trail run at Goddard Park on September 26, 2026 featuring fields and wooded trails along Greenwich Bay, open to all ages with age group awards.
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 community 5K and 1 mile fun run on October 11, 2026 supporting Unified programs at Beckwith and Dighton Middle Schools. Fees vary by registration period and registered runners receive T-shirts and awards for top finishers.
A 3 mile trail run through Sakonnet Vineyard in Little Compton followed by dinner, wine and music among the vines. Race entry includes timing, a t shirt and a souvenir wine glass; dinner only options are also available.
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 14th annual community 5K in Wareham, MA on October 31, 2026 held at AD Makepeace with adult and youth registration categories and published fees.