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

There are 9 running races in Annapolis, Maryland in 2026. The next is the Escape Through The Cape on April 11. Distances include 5K races, 10K races, half marathons.

Escape Through The Cape

Sat, Apr 11 · Annapolis, MD Annapolis

Road 1 Mile Fun Run (non-timed event)5k Run/Walk

From $30 Open Closing Soon

Sandy Point State Park - Happy Little 5K

Sat, Apr 18 · Annapolis, MD Annapolis

Road 5K Race Entry (NO race swag included)

From $25 Open Closing Soon

22 Miles to Break Boundaries- 24 Hour Ultra Trail

Sat, May 16 · Annapolis, MD Annapolis

Ultra 24 Hour Trail Run

From $150 Open

"Copper the Bloodhound's K9 Miler RUCK/Hike" Benefitting Chesapeake K9 Fund

Sat, Jun 6 · Annapolis, MD Annapolis

Copper the Bloodhound's K9 Miler Ruck

From $30 Closed

Annapolis Striders John Wall Memorial One Mile Track Run

Sat, Jun 27 · Annapolis, MD Annapolis

Road Annapolis Striders John Wall Memorial One Mile Track Run

From $15 Open

Annapolis 10 Mile Run

Sun, Aug 30 · Annapolis, MD Annapolis

Road Ten Mile Run

From $65 Open

Bay Bridge Paddle

Sun, Sep 13 · Annapolis, MD Annapolis

Triathlon The Soft Shell Kayak DoubleSoft Shell Kayak plus 1 mile beach runThe Soft Shell Kayak +15

From $50 Open

Annapolis RUN for The Light House

Fri, Sep 18 · Annapolis, MD Annapolis

Virtual 1 Mile Walk (In-Person)5k (In-Person)5K (Virtual) +2

From $25 Open 32 spots left

Naptown Half Marathon & 10K/5K

Sat, Dec 19 · Annapolis, MD Annapolis

Road 5K10KHalf Marathon

From $40 Open