Pain in De Ass 5K

Get ready for a memorable dash at the Pain in De Ass 5K, set for Sunday, June 7, 2026, in the charming town of Chesapeake City, Maryland. This 5K race promises an experience that blends scenic beauty with a lively celebration. The course offers picturesque views, guiding runners along the historic C & D Canal and winding through Chesapeake City's charming streets, culminating in a spectacular finish near the sparkling Chesapeake Bay.

Runners can anticipate typical race day conditions in early June, with highs around 80F and lows around 61F, and a modest 17% chance of precipitation. Beyond the scenic run, what truly sets the Pain in De Ass 5K apart is its renowned post-race party. Participants are invited to an unforgettable celebration held on the deck of the Chesapeake Inn, located at 605 Second Street, where they can enjoy a complimentary "Pain in De Ass" signature drink (for those 21 and over).

Every finisher will be rewarded not only with bragging rights but also with an exclusive Pain in De Ass 5K shirt and a commemorative finisher medal. The race kicks off at 9:00 AM sharp near the bandstand on 1st Street, promising a lively start and an engaging atmosphere that runners consistently praise. This event is a perfect blend of fitness, community spirit, and unique post-race festivities.