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Chick & Ruth's Delly - Annapolis, MD
Challenge: The patriotic folks at Chick & Ruth's pledge the flag every morning. Equally American are the portions, with four major challenges waiting for you: the 6-pound Colossal Milkshake, the Super-Colossal 3-pound sandwich (shown above; choice of two meats, yay!) and the Super-Duper Colossal 3-pound cheeseburger challenge (getting woozy). Cost for the 3-pounder: $26.99.
Your Reward: Your mug shot on the Chick & Ruth's website.
Damage Guesstimate: 3,880