When are most 5K races held in Annapolis?
September is the busiest month for 5K races in Annapolis, with 3 of the 5. If you are flexible on the date, that is the quickest way to narrow things down.
Maryland · 5K
5K Races in Annapolis, Maryland
Every upcoming 5K around Annapolis, with start times, entry fees, finish-time stats from past editions, start-line maps, and the local run clubs to train with.
5 upcoming 5K races found · 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 $23Details Sun, Sep 13, 2026The Peake Run 60th Anniversary Run Annapolis, MDFrom $35Register Fri, Sep 18, 2026Annapolis RUN for The Light House Annapolis, MDFrom $50Details Sat, Dec 19, 2026Naptown Half Marathon & 10K/5K Annapolis, MDFrom $40Details Sat, Mar 20, 2027Annapolis Running Festival Annapolis, MDFrom $45Details
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 Jul 27, 2026.
Common Questions About Running a 5K in Annapolis
How much do Annapolis 5K races cost?
Entry fees for 5K races here run from $23 to about $50, depending on the event and how early you register.
How early should I register for a 5K in Annapolis?
3 of the 5 5K races in Annapolis already have a price increase scheduled, so entry gets more expensive the longer you leave it. Race pricing almost always steps up as the date approaches, and signing up early is usually the cheapest option.
Are Annapolis 5K races beginner-friendly?
Yes, for the most part. Across the 4 5K races in Annapolis with published results, the typical median finish is around 36:47, 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 5K in Annapolis?
Browse Annapolis run clubs on RunSesh to find a training group at your pace.
Are there trail 5K 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.