Kennebunkport
Trail Running Calendar near Kennebunkport 2026-2027
Explore the top trail runs near Kennebunkport for 2026-2027! We've gathered 12 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.
Trail Fest in Arundel offers 5k, 10k and half marathon courses on the ACT and Eastern Trails, with medals, shirts, a kids bike race, live music and food.
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 32.5 mile five lap trail ultra in Windham, ME on Red, Blue and Purple trails with two aid stations per loop and volunteer support.
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
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.
July 2027
Back Cove Backyard Ultra in Portland ME features roughly 4.16 mile hourly loops on the Back Cove Trail repeated until one runner remains.