Rehoboth
Trail Running Calendar near Rehoboth 2026-2027
Explore the top trail runs near Rehoboth for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
10 km trail race in Milton MA on 10/11/2026 featuring a moderately technical, low elevation course; registration runs 9/25 to 10/11, fee $20.
A trail run through Sakonnet Vineyard on October 17, 2026 with an approximately 3 mile course and post-run wine, dinner and music.
A six hour weighted trail race in Mansfield MA where competitors carry and adjust weight each lap and score by pound miles called Kz.
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 harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.
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 stadium stair-climb at Gillette Stadium raising funds for Homes For Our Troops, covering about 5,184 steps in the lower bowl with individual, team, and fundraising options.
A continuous 50-mile trail race on a 3.1-mile loop in Wrentham, MA, with chip timing, a 12-hour cutoff, and a 75-runner field limit.
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.
Trail half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.
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.
Thanksgiving morning Turkeywacker 5K in Wrentham MA on 11/26/2026 featuring a scenic trail, post-race donuts and cider, raffle prizes, and awards by division.
January 2027
Winter trail event at Hale Education in Westwood with a 30 hour ultra and a 15 mile looped course, marked trails, cupless aid stations, and required cold weather gear.