Running Races in Annapolis, Maryland 2026 | Browse All Races | My Next Race

There are 11 running races in Annapolis, Maryland in 2026. The next is the RTB Fair Winds 5k/Fun Run on October 24. Distances include 5K races, half marathons, 10K races.

RTB Fair Winds 5k/Fun Run

Sat, Oct 24 · Annapolis, MD Annapolis

Virtual 4th Annual 5K/Fun RunRTB Fair Winds Virtual 5k/Fun Run

From $15 Open

Bay Bridge Run

Sun, Nov 8 · Annapolis, MD Annapolis

Virtual Back in Time 2023 Virtual Run10K- Charity RegistrationVirtual 10K- Charity Registration +10

From $0 Open

Bay Bridge Walk/Run for a Cause - Walk the Walk Foundation

Sun, Nov 8 · Annapolis, MD Annapolis

Road 10K - Walk the Walk Participant

From $70 Open

Navy Football-Bay Paddle Tailgate

Sat, Nov 21 · Annapolis, MD Annapolis

Navy Football-Bay Paddle Tailgate

From $40 Open

Annapolis Turkey Trot

Thu, Nov 26 · Annapolis, MD Annapolis

Road Turkey Trot 5K

From $50 Closed

St. Mary's Boys Basketball Annual 5K Run and 1-Mile Fun Run

Sun, Nov 29 · Annapolis, MD Annapolis

Road St. Mary's Boys Basketball Annual 1-Mile Fun RunSt. Mary's Boys Basketball Annual 5K Run

From $30 Open

DeCesaris Prout Cancer Foundation - Jingle Bell 5K/3K

Sat, Dec 5 · Annapolis, MD Annapolis

Road 3K Walk5K Run

From $50 Open

Anniversary Run 15K

Sun, Dec 13 · Annapolis, MD Annapolis

Road 2026 Anniversary Run 15K

From $15 Open

Naptown Half Marathon & 10K/5K

Sat, Dec 19 · Annapolis, MD Annapolis

Road 5K10KHalf Marathon

From $40 Open

Annapolis Running Festival

Sat, Mar 20 · Annapolis, MD Annapolis

Virtual Virtual 5K - Charity RegistrationVirtual 5K - Charity RegistrationVirtual 5K +27

From $0 Open

Annapolis RUN for The Light House

Fri, Sep 10 · Annapolis, MD Annapolis

Virtual 1 Mile Walk (In-Person)1 Mile Walk (In-Person)5K (Virtual) +7

From $25 Closed 32 spots left