Odessa
Trail Running Calendar near Odessa 2026-2027
Explore the top trail runs near Odessa for 2026-2027! We've gathered 23 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 and family festival at Old Stone Cider with a food drive, live music, vendors, costume contests, and fundraising for 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.
Donation based trail run and walk at Brandywine Creek State Park with marked 5 and 10 mile courses; proceeds benefit local youth cycling and park groups.
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.
A self-timed 5 miles loop in Bel Air that starts and finishes at Southampton Middle School and follows part of the Bel Air Town Run Course.
Open 5K cross country championship at Brandywine Creek State Park on November 28, 2026, with registration fees and proceeds supporting a local high school shoe program.
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.
A club 5 km run and walk on the new section of the Ma and Pa Trail from North Avenue Trailhead in Bel Air with self-timing and on-site merchandise.
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 single-loop hike at Fair Hill NRMA on May 22, 2027, with aid stations, a finisher medal, and roughly 1,600 ft of elevation gain.
5K at Harvest Ridge Winery crossing MD and DE through vineyards, wooded trail and country road, with live music, a food truck and complimentary wine and keepsakes.
A scenic chip timed 5K through two vineyard properties in Woodstown NJ on May 23, 2027 with awards, postrace music, and a complimentary glass of wine for those 21 and older.
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.