Pain in De Ass

JUN
7
2026
Run along the scenic C and D Canal in Chesapeake City before enjoying a post race celebration and signature drink on the deck of the Chesapeake Inn.
Sun 7 Jun 2026
5 kilometers

Always double-check with the organizer's website! This page may contain affiliate links.

Event Overview

The Pain in De Ass 5K takes place in the town of Chesapeake City, Maryland. This event features a running course that starts and finishes near the waters of the Chesapeake Bay. Participants follow a route that leads along the C & D Canal and through the local town area.

The event offers a single distance for all registered runners:

  • 5 km

Participant Experience

All participants receive a commemorative event shirt and a finisher medal upon completing the course. The race utilizes chip timing for age group results and gun timing for overall and masters categories. Awards are presented to the top male and female finishers in the overall and masters divisions, as well as the top three finishers in multiple age brackets ranging from 13 and under to 70 and over.

Post-Race Activities

Following the run, an organized gathering is held on the deck of the Chesapeake Inn at 605 Second Street. The post-race event includes entertainment and snacks. Participants aged 21 and over are provided with one complimentary signature drink. The event also serves as a collection point for the CCEA Food Pantry, and runners are encouraged to bring donations such as breakfast items, canned meats, or personal care products. Street parking is available throughout the town of Chesapeake City for those attending the event. Visit the organization's website for the most recent information.

5 km