Pain in De Ass

JUN

7

2026

The Pain in De Ass 5K winds through historic Chesapeake City and along the scenic C & D Canal. Every runner gets a shirt, a finisher medal, and a signature drink. The event finishes with a post race party on the deck of the Chesapeake Inn.

Sun 7 Jun 2026

Chesapeake City, Maryland

Registration

5 kilometers

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Event Information

The Pain in De Ass 5K takes place in Chesapeake City, Maryland on Sunday, June 7, 2026. The event starts and finishes near the waters of the Chesapeake Bay.

The race course runs along the C & D Canal and through the town.

Participant Perks

All participants will receive an event shirt and a finisher medal. Each participant will also receive one complimentary signature drink. A post-race party with snacks and entertainment will be held on the deck of the Chesapeake Inn.

Registration and Details

Registration and bib pick-up is available on race day at the Chesapeake Inn from 8:00 AM until 8:45 AM. The race start time is 9:00 AM near the bandstand on First Street.

Parking is available on the streets in Chesapeake City. Visit the organization's website for the most recent information.

5 km

Pain in de Ass 5k