Annapolis
Trail Running Calendar near Annapolis 2026-2027
Explore the top trail runs near Annapolis 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.
September 2026
A 10K road race and a 5K road/trail combo at the Shrine of St Anthony in Clarksville, MD on Sept. 5, 2026. Both USATF certified with chip timing, guaranteed shirts for early registrants, music and family activities.
A 5K and half marathon in Georgetown, Washington, DC on September 12, 2026 along the Chesapeake and Ohio Canal path with in-person and virtual options.
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 Georgetown running event on September 20, 2026 featuring a Half Marathon and a 5K on the Chesapeake and Ohio Canal path, with virtual options and walkers welcome.
Annual 5K trail run and family fun run at Terrapin Nature Trail on Maryland's Eastern Shore with a separate 1 mile kids run.
Scenic races on the Chesapeake & Ohio Canal in Georgetown on September 27, 2026, offering a 5K, a half marathon and virtual entry options.
October 2026
A run crew led event in Washington, DC offering 5K, 19K and 19 mile routes that use both road and trail sections across the city.
USATF certified marathon and half on the flat C&O Canal Towpath at Fletcher's Cove with aid stations, finisher medals, and cash prizes.
A 4th annual 5K and virtual fun run at Quiet Waters Park with paved trails, costume contests, and proceeds supporting scholarships and camp aid for children.
November 2026
Trail races of 50K and 20K at Rosaryville State Park near Upper Marlboro MD on wooded single track loops with aid stations, drop bags, and postrace food and fires.
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.
A 25K trail race in Queen Anne MD on November 21 with mostly single track, three stocked aid stations, variable trail conditions, organized by Algonquin Ultras.
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 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
A December running event in Washington DC featuring 5K, half marathon and marathon courses along the Chesapeake and Ohio Canal plus virtual entry options.
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.
January 2027
A Georgetown running event on January 17, 2027 offering a 5K and a half marathon along the Chesapeake and Ohio Canal path with virtual options.
5K and 10K races in Stevensville, MD, on varied terrain with forest, sand, Chesapeake Bay Bridge views, and a post-race drink option at a nearby brewery.