What race distances can I run in Annapolis?
Annapolis has 5K (8), 10K (5), Half Marathon (3). The 5K is usually the easiest entry point if you are new, and the links above jump straight to each distance.
Maryland · Race calendar
Running Races in Annapolis, Maryland
Upcoming running races in and near Annapolis, Maryland - 5Ks, 10Ks, half marathons and more, with dates, pricing, finish-time stats, start-line maps, and local run clubs to train with.
10 upcoming races · 4 with finish-time stats
By the numbers
The Biggest and Longest-Running
The Annapolis races that stand out on the numbers: the biggest field, and the longest unbroken run of editions.
Sun, Sep 13, 20269/11 Heroes Run - Annapolis Annapolis, MDFrom $26Details Sun, Sep 13, 2026The Peake Run 60th Anniversary Run Annapolis, MDFrom $35Register Fri, Sep 18, 2026Annapolis RUN for The Light House Annapolis, MDFrom $60Details Sat, Oct 24, 2026RTB Fair Winds 5k/Fun Run Annapolis, MDFrom $35Details Sun, Nov 8, 2026Bay Bridge Run Annapolis, MDFrom $80Details Sun, Nov 8, 2026Bay Bridge Walk/Run for a Cause Annapolis, MDFrom $100Details Thu, Nov 26, 2026Annapolis Turkey Trot Annapolis, MDFrom $50Details Sun, Nov 29, 2026St. Mary's Boys Basketball Annual 5K Run and 1-Mile Fun Run Annapolis, MDFrom $30Details Sat, Dec 19, 2026Naptown Half Marathon & 10K/5K Annapolis, MDFrom $40Details Sat, Mar 20, 2027Annapolis Running Festival Annapolis, MDFrom $50Details
How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Sep 10, 2026.
Common Questions About Racing in Annapolis
When is race season in Annapolis?
November is the busiest month for races in Annapolis, with 4 of the 10, followed by September with 3. If you are flexible on the date, that is the quickest way to narrow things down.
Are Annapolis races beginner-friendly?
Yes, for the most part. Across the 4 races in Annapolis with published results, the typical median finish is around 1:08:52, which means half of every one of those fields came in slower than that. Recreational runners and walk-runners are the bulk of these fields, not the exception.
Where can I train for a race in Annapolis?
Browse Annapolis run clubs on RunSesh to find a training group at your pace.
Are there trail races near Annapolis?
Yes, 2 races around Annapolis get you off the pavement: 2 mix road and trail. Surfaces are not always published, so it is worth checking a specific race before you register.