Odessa
Trail Running Calendar near Odessa 2026-2027
Explore the top trail runs near Odessa for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A short yoga session followed by a chip timed 5K at Penns Woods Winery in Chadds Ford, featuring a vineyard course, race shirts, postrace music, and a wine option for 21 plus.
Trail runs, a 2 mile walk and a kids race at Ramsey's Farm in Wilmington with proceeds supporting 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
Trail races at Glenroy Preserve on October 4, 2026: 5 mile, 25K, and 50K loops with creek crossings, 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.
A Harford County Running Club Sunday run in Havre de Grace with a self timed, stroller friendly 4 mile road course and optional extra mileage around a hay field.
A Halloween 5K trail run at Old Stone Cider with costumes encouraged, live music, vendors and a food drive benefiting the Chester County Food Bank.
November 2026
Enjoy a 5k run or walk from the lighthouse at Concord Point Park as part of the Harford County Running Club Sunday Run Series.
A third annual charity trail event at Brandywine Creek State Park with 5 mile and 10 mile options; proceeds support Delaware cycling and park organizations.
A scenic 5K at Milburn Orchards in Elkton on November 8, 2026, across orchard and farm trails with a portion of proceeds donated to local organizations.
A self timed 5k from Made Me Mine in Abingdon with walking option, stroller friendly course and parking at Constant Friendship Shopping Center.
A 5 km on the Mason-Dixon Trail in Darlington with two multi-loop challenge options and self-timed results, free registration.
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.