Running Races in Annapolis, Maryland
9 upcoming races in Annapolis, updated nightly. For radius search from your exact zip, use the Race Finder.
Racing in Annapolis: what the calendar looks like
There are 9 upcoming races on the Annapolis calendar over the next 12 months, with race dates in 5 of the next 12 months. Among complete calendar months, December 2026 has the most listed races, with 3. By race count, Annapolis ranks 7th among Maryland cities.
Of those, 8 offer a 5K, 3 offer a Half Marathon and 2 offer a 1 Mile. The next half marathon is Naptown Half Marathon & 10K/5K on December 19. Where fees are published, the median entry in Annapolis is $35, above the Maryland median of $30.
Close enough for a race-day drive: Laurel (10 races, 23 miles), Baltimore (23 races, 25 miles), Columbia (12 races, 26 miles).
Races by month
- Nov 20263 races
- Dec 20263 races
- Feb 20271 race
- Mar 20271 race
- Sep 20271 race
November 2026
- Thu 11/26Annapolis Turkey TrotAnnapolis, MD · 5K · from $50 · register ↗
- Sun 11/292026-2027 ET's Jesters Winter 5k ClassAnnapolis, MD · 5K · register ↗
- Sun 11/29St. Mary's Boys Basketball Annual 5K Run and 1-Mile Fun RunAnnapolis, MD · 5K · 2K · from $30 · register ↗
December 2026
- Sat 12/5DeCesaris Prout Cancer Foundation - Jingle Bell 5K/3KAnnapolis, MD · 5K · 3K · from $50 · register ↗
- Sun 12/13Anniversary Run 15KAnnapolis, MD · 15K · from $15 · register ↗
- Sat 12/19Naptown Half Marathon & 10K/5KAnnapolis, MD · Half Marathon · 10K · 5K · from $40 · register ↗
February 2027
- Sat 2/13Cupid's Chase 5K AnnapolisAnnapolis, MD · 5K · from $40 · register ↗
March 2027
- Sat 3/20Annapolis Running FestivalAnnapolis, MD · Half Marathon · 10K · 5K · from $30 · register ↗
September 2027
- Fri 9/10Annapolis RUN for The Light HouseAnnapolis, MD · Half Marathon · 5K · 1 Mile · from $29 · register ↗
Where to stay in Annapolis
Race-weekend hotel search, dates prefilled for check-in the night before.
- Dec 19Naptown Half Marathon & 10K/5KFind hotels for this race weekend
- Mar 20Annapolis Running FestivalFind hotels for this race weekend
- Sep 10Annapolis RUN for The Light HouseFind hotels for this race weekend
Hotel links are affiliate links. Booking through them costs you nothing extra and helps keep RunRace USA free.
Planning a race
- Getting inlotteries, qualifiers, and how entry works for the races that sell out
- Lottery watchwhich race lotteries and registration windows are open right now
- Choosing a first marathona practical guide to picking a debut race