Running Races in Chesapeake City, Maryland 2026 | Browse All Races

There are 3 running races in Chesapeake City, Maryland in 2026. The next is the Pain in De Ass 5K on June 7. Distances include 5K races.

Sun, Jun 7 · Chesapeake City, MD Chesapeake City

Road Pain in De Ass 5K

From $35 Open

Sat, Aug 1 · Chesapeake City, MD Chesapeake City

Road 5K Trail Run8K Trail Run

From $44 Open

Sun, Aug 30 · Chesapeake City, MD Chesapeake City

Road Crush the Chesapeake 5K

From $25 Open

Running Races in Chesapeake City, Maryland — 2026