Rye
Trail Running Calendar near Rye 2026-2027
Explore the top trail runs near Rye for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.
Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.
A single-day multisport festival at Pawtuckaway State Park offering swim, trail bike and run options, open to people who identify as women and benefiting Girls on the Run NH.
October 2026
A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026, with proceeds supporting the Kennebunkport Conservation Trust.
Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.
A rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.
October 18 trail race in Gloucester, MA through Ravenswood Park on single track and carriage roads, 4.1 miles; online registration closes Oct 15 and race day registration is available.
A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.
Holistic Hustle in Kennebunkport features a timed 5K, a trail 10K and a kids half mile fun run at Emmons Preserve on October 31, 2026. The community fundraiser includes music, family activities, finishers medals and a raffle.
A costumed 5K trail run at Wells Reserve at Laudholm on October 31, 2026, supporting coastal conservation with timing, water stations, T-shirts, and awards.
November 2026
A November trail festival at Willowdale State Forest offering races from 10K to 100K, a cider donut mile, and a free youth fun run.
March 2027
April 2027
A chip timed 5K trail race and kids fun run at Odiorne Point State Park supporting Marine Mammal Rescue, with race shirts, age group prizes, and a post race beach cleanup.