Odessa
Trail Running Calendar near Odessa 2026-2027
Explore the top trail runs near Odessa for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A self-timed loop-trail event in Havre de Grace on 08/30/2026 with a listed distance of 3 miles. Runners have 90 minutes to complete as many loops as they like; parking is at Steppingstone Farm Museum.
September 2026
A winery event pairing a short yoga session with a chip-timed 5K on vineyard grass, race swag, a wine glass for 21+ participants, live music, and age group awards.
Community charity event at Ramsey's Farm in Wilmington with a 15k trail loop, 5k, 2-mile health walk and a kids fun run, benefiting local Delaware charities.
A community 5K and 1 mile kids run in West Grove PA on September 26 2026 supporting Avon Grove High School cross country with a three-loop grass course and race-day refreshments.
A dog friendly fundraising event at Bellevue State Park on September 27, 2026 featuring a scenic 5K and a one mile Mutt Mile, with race timing, awards for dogs and people, vendors, a costume contest, and merchandise.
October 2026
Loop trail races at Glenroy Preserve offering 5 mile, 25K, and 50K courses with technical terrain, multiple creek crossings, four aid stations, and post race food and beer.
Trail races at Parvin State Park offer a half marathon and a 6 hour lap event on a mostly trail lollipop loop. The event is cupless and uses an aid station at the start and finish.
December 2026
A 5K cross-country run at Sharp Farm in Middletown on Dec 5, 2026, across fields, forest edges and wide trails with proceeds supporting Delaware Wild Lands.
January 2027
March 2027
A spring trail 50K at Susquehanna State Park with two identical loops, about 4,300 feet of climbing and several stream crossings, supported by aid stations and volunteers.
April 2027
A turtle themed 5K at Hopkins Farm Brewery in Havre De Grace raising funds and awareness for the Susquehannock Wildlife Society. The trail race includes wooden participant medals, costume prizes, and an after party with live music.
May 2027
A morning 5K held as part of the Fair Hill Scottish Games on May 15, 2027, in Elkton, MD, with on-field entries accepted, an entry fee that includes admission, and cash prizes plus trophies for top finishers.
A 20 mile loop through Fair Hill Natural Resources Area on May 22, 2027 with aid stations, a finisher medal and complimentary on site parking.
June 2027
Five consecutive race days June 2–6, 2027 across DE MD PA NJ and NY offering marathon, half, 50K, 10K and 5K with daily aid stations and collectible medals.