Annapolis
Trail Running Calendar near Annapolis 2026-2027
Explore the top trail runs near Annapolis for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Marathon and half marathon on the C&O Canal Towpath at Fletcher's Cove in Washington DC with a mostly flat Boston qualifying course and age group awards.
November 2026
Trail races of 50K and 20K through the single-track woods of Rosaryville State Park near Upper Marlboro, MD, organized by the Annapolis Striders with limited field and aid stations.
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, 2026 with mostly single track terrain, three aid stations, awards for top finishers, and no rain date.
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 5k in Georgetown along the C&O Canal with chip timing, a long-sleeved technical shirt and finisher medal; virtual option and series points available.
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 at Langston Golf Course and the Anacostia Tidal Marsh offering a 3K loop and a 1K fun run with proceeds supporting a local charter school.
December 2026
Three distances on the C&O Canal path in Washington, DC, with chip timing, finisher medal, a virtual option, and series points for multiple race series.
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
A scenic Georgetown event with a half marathon and 5k on the C&O Canal path, offering chip timing, finisher medals, and a virtual option.
Scenic gravel 5k and 10k at Terrapin Nature Park with chip timing, finisher medal, virtual option, and a drink ticket for Cult Classic Brewing.
February 2027
March 2027
Scenic, flat half and full marathons along the Chesapeake and Ohio Canal in Georgetown with chip timing, finisher medal, technical shirt, and a Boston qualifying full marathon option.
April 2027
A Georgetown race on the C&O Canal offering 5k, 10k and half marathon distances with chip timing, medals, technical shirts and a virtual option.