Annapolis Running Festival

MAR
21
2026
Join the Chessie Challenge, a multi race series centered on the Annapolis Running Festival with Half Marathon, 10K and 5K plus two more Maryland races. Register all three races for a $15 bundle discount and extra swag including an interactive medal with a turnable dial and a custom terrycloth chair cover.
Sat 21 Mar 2026
Half Marathon 10 kilometers 5 kilometers

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

Event overview

The Chessie Challenge is a multi-race series organized by Corrigan Sports. It is tied to the Annapolis Running Festival and to two additional Maryland races in 2025. The Annapolis Running Festival offers the following distances:

  • Half-Marathon
  • 10K
  • 5K

Challenge entry and rewards

To enter the Chessie Challenge participants must register for three races: any distance at the Annapolis Running Festival, any distance at the Baltimore 10-Miler (June 7, 2025) or the Baltimore Running Festival (October 18, 2025), and any distance at the Ocean City Running Festival (November 1, 2025). Registrants receive the regular premiums and medals for each race plus additional Chessie Challenge items.

Challenge-specific benefits for 2025 include a $15 bundle discount when registering with the BUNDLE option (the site applies $5 off each race), an extra interactive Chessie Challenge medal with a turnable dial that reveals locations, and a custom logoed terrycloth chair cover. The page also notes discounts on other Corrigan Sports events and that participants registering separately must use an online form to merge entries to receive official challenge entry and benefits. Visit the organization's website for the most recent information.

Half Marathon
Half-Marathon
10 km
10k
5 km
Chessie Challenge

Events nearby