If you are looking for races in Annapolis, Maryland, you have come to the right place. Annapolis has a growing running scene with 13 races listed in our directory, including 4 upcoming events in 2026. Whether you are lacing up for your first 5K or chasing a new personal record, there is something here for every runner.
Upcoming Races in Annapolis, Maryland
Here is a look at the top upcoming races in Annapolis this year. We update our listings weekly so you always have the most current information.
Annapolis 10 Mile Run
Date: August 30, 2026
Lace up for a beautiful 10-mile run that takes you through historic Annapolis and over the Severn River, organized by the Annapolis Stridersa volunteer-powered 1000-member nonprofit dedicated to community fitness since 1978. Read full details →
Bay Bridge Paddle
Date: September 13, 2026
Join us for this exciting paddlesports celebration on the Chesapeake Bay, where you’ll find the perfect distance and boat type for your skill levelwhether you’re paddling a kayak, SUP, surfski, or outrigger canoe across The Span (9 miles), The Steamer (3 miles), or The Soft… Read full details →
9/11 Heroes Run – Annapolis
Date: September 13, 2026
Join us in Annapolis for a 5K that brings together runners, walkers, and ruckers of every ability to celebrate the courage of 9/11 heroes and our nation’s service members. Read full details →
Annapolis RUN for The Light House
Date: September 18, 2026
Get ready to run for a cause in beautiful Annapolis! Choose between a half-marathon or 5k as you enjoy scenic trails through Quiet Waters Park and the charming Chesapeake Bay-front area of Hillsmere Shores. Read full details →
Why Run in Annapolis?
Running events in Annapolis offer a mix of community fun runs, charity 5Ks, and competitive road races throughout the year. The local running community is active and welcoming to runners of all levels — from first-timers to seasoned racers. Many of these events benefit local charities and organizations, making race day about more than just your finish time.
Find More Races in Maryland
Annapolis is just one part of a thriving Maryland running scene. If you want to explore more events across the state, check out our full race listings for Maryland — we track every upcoming running event from 1 mile fun runs to full marathons.
Get Ready to Race
Found a race you want to run? The next step is making sure you are properly trained for it. Whether you are a first-timer aiming to finish or a veteran chasing a PR, having the right training plan makes all the difference.
Take our free 3-question training plan quiz and get matched to the right plan for your fitness level in under a minute. We will send it straight to your inbox so you can start training today.
Good luck out there — see you at the finish line in Annapolis!
