Annapolis
Trail Running Calendar near Annapolis 2026-2027
Explore the top trail runs near Annapolis for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail races in Rosaryville State Park on November 14, 2026 offering 50K and 20K on mostly single track with aid stations, drop bags, and time limits.
A free BRRC 5K cross country at Herring Run Park on November 15, 2026, with an XC style start, mixed surfaces, river crossings, and volunteer-supported turns.
25K trail race in Queen Anne, MD on November 21, 2026 with mostly single track, three stocked aid stations, awards for top finishers, and no refunds if canceled.
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 chip timed Thanksgiving 5k in Georgetown along the scenic C&O Canal with a technical shirt, finisher medal, and a virtual race option.
A Thanksgiving Day 5K at Eastern Regional Park in Middle River with two laps on mixed paved and natural paths and registration options that include a hat and medal.
A community Thanksgiving run in Washington, DC with 3K and 1K courses through the Anacostia Tidal Marsh supporting Two Rivers Public Charter School.
December 2026
Three races on the C&O Canal in Georgetown and Fletcher’s Boathouse: 5K, half marathon and a Boston qualifying full marathon with chip timing and medals.
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
January 17, 2027 race in Georgetown offering a half marathon and 5k on the C&O Canal path with chip timing, medals, shirts, and a virtual option
Gravel-trail 5K and 10K at Terrapin Nature Park on January 23, 2027, with chip timing, water views, series points, and a post-race drink at Cult Classic Brewing.
February 2027
A 50k trail race at Rockburn Branch Park on February 6, 2027, run as six wooded loops with relay teams of two to six and a stocked aid station.
March 2027
Scenic flat half and full marathon in Georgetown along the C&O Canal with chip timing, water stations, a virtual option, and series points.
April 2027
Multi distance, chip timed races in Georgetown along the C&O Canal featuring medals, technical shirts, water stations, and a virtual option.
May 2027
USATF certified marathon and half on the C&O Canal Towpath at Fletcher's Cove with aid stations, finisher medals, technical shirts, and cash prizes.