Annapolis
Trail Running Calendar near Annapolis 2026-2027
Explore the top trail runs near Annapolis for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Open 6k at Terrapin Nature Park in Stevensville, MD on September 19, 2026; open to all, $25 entry, flat sandy gravel course with bay views.
A half marathon and 5k on the C&O Canal in Georgetown and Fletcher’s Boathouse with chip timing, medals, a virtual option, and series points.
Annual 5K trail run and family fun run at Terrapin Nature Trail on Maryland's Eastern Shore with a separate 1 mile kids run.
A double-loop 5k trail in Washington, DC on September 26, 2026 benefiting St. Anselm's Abbey School's memorial scholarship fund with awards for overall and age-group finishers.
A chip-timed half marathon and 5K along the C&O Canal in Georgetown and Fletcher’s Boathouse, with medals, technical shirts, a virtual option, and proceeds benefiting Team RWB DC.
October 2026
A community-led run in Anacostia, DC offering 19 Mile, 19K and 5K on an unsanctioned road and trail course with race shirt, medal, and festival.
USATF certified marathon and half on the flat C&O Canal Towpath at Fletcher's Cove with aid stations, finisher medals, and cash prizes.
November 2026
Experience the natural beauty of Rosaryville State Park at this classic single track trail race featuring 50K and 20K distances through wooded meadows and rolling hills.
Free BRRC GPS 5K at Herring Run Park featuring mixed paved, field and single track terrain, two river crossings, and course variations from local high school routes.
Experience the beauty of Maryland trails with the Tuckahoe 25k, a scenic race through single track paths and horse trails featuring fully stocked aid stations and festive churros.
Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.
A Thanksgiving morning 5k in Georgetown along the C&O Canal with chip timed results, finisher medal, long sleeve technical shirt, a virtual option and series points.
A Thanksgiving morning 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural trails; open to all ages, $15 registration fee.
December 2026
Multi-distance holiday race on the C&O Canal path in Georgetown and Fletcher’s Boathouse with in-person and virtual options and charity partnership.
Eight hour trail endurance race at Terrapin Nature Park where each 2.8 mile lap fills a participant stocking with surprises and top finishers earn awards.
A 15K trail race at Quiet Waters Park in Annapolis on December 13, 2026, part of the Championship Series with special rates for Striders members and race day registration.
January 2027
Scenic C&O Canal races in Georgetown offering a chip timed half marathon and 5K with medals, technical shirts, a virtual option and series points.