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Annapolis Running Festival

March 2025 (Date TBD) Annapolis, MD 21401 US

Chessie Challenge




Aye, Aye Matey!   If you have been in these parts for a while like I have, then you know the legend of Chessie.  Chessie is the mythical sea monster that trolls the Chesapeake Bay and has been part of sailor lore for a lifetime [Learn More ].  I have been sailing these waters since I was a wee lad and ne’er set an eye on her.  Oh, but I have heard the tales!  

My crew and me are setting out on a journey to find this Chessie.  We’re looking for a few more deckhands if you are up for an adventure.  We pay handsomely too—a few shiny medals and other lavish gifts await you.  It’s a long voyage, about 7 months, but if you have the sea legs for it, we welcome you aboard!

As I say, I haven’t seen her myself, but some say Chessie has green eyes and will swallow your ship whole.  Others say she is a docile creature who saves sailors that fall overboard and protects the Bay from evil.   I don’t know what to believe but I do know one thing—we need all the help we can get to track her down and see what she is really about.

Rumor has it that she lies in the calms of the Severn River near Annapolis during the winter.  She awakens from her hibernation come springtime to begin feeding once the landlubbers start pretending to be mariners near Ego Alley.

Once she’s had her fill there she travels north and spends quite a while in the Patapsco rummaging near Ballmer- sorry Bal – TEE – More.  Some say she is there from June until October.

As the season turns, it’s been told that she heads south to the mouth of the Bay and out into the mighty Atlantic.  Quite a few sightings in the Isle of Wright Bay in late fall.  Lots of times she’s seen in the waters outside Seacret’s but I think its something else making those images appear if you know what I mean.

We have a solid navigational plan and think we can track her down with your help.  We hope you will come along on our odyssey and be part of the great Chessie Challenge of 2024!

To enter the Chessie Challenge participants are required to register for the following:
1)     Any distance at the Annapolis Running Festival (March 9, 2024 or virtually)
2)    Any distance at the Baltimore 10-Miler (June 3, 2023) OR the Baltimore Running Festival (Oct 19, 2024)
3)    Any distance at the Ocean City Running Festival (Nov. 2, 2024)

In addition to all of the premiums, medals and other amenities for participating in each race, Registrants of the Chessie Challenge will receive:
•    $15 off the entry fee for the bundle – $5 off each race is taken automatically when you register using the BUNDLE option*
•    An extra Chessie Challenge medal - The medal is a large 5.5" design and pictures lovable Chessie swimming in the Bay.  The water will be true-to-life and depicted with a glittery liquid fill that will allow you to splash away with Chessie!
•    A custom logoed Chessie Challenge beach bag cooler- This 600 Denier Polyester cooler bag is a large size-  19"L x 6"W x 12"H to be exact.   Its zippered insulated main compartment holds 20 cans plus ice.  It also has a front pocket and a 9.5" handle drop height.  (offered in blue or black on a first come first serve basis.)
•    Discounts on other CSE events and other benefits along the way 

*Must register using the BUNDLE OPTION to receive the discount.  Those registering for the races separately must use the online form to merge their entries and receive entry into the challenge.


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