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Chick and Ruth's Annapolis
Chick and Ruth's Annapolis

The Colossal Food Challenges of Annapolis

Do you have what it takes to join the ranks of the elite? At Chick and Ruth's Delly, we don’t just serve food; we serve legends. For years, we’ve been the home of the most famous food challenges in Maryland, as featured on Man v. Food.

Whether you’re eyeing our massive 3lb sandwiches or the infamous 6lb milkshake, these challenges are a test of will, stomach capacity, and Annapolis pride. Conquer the mountain, and you’ll walk away with more than just a full stomach, you’ll earn an exclusive finisher’s T-shirt, a spot on our Social Media Wall of Fame, and the eternal respect of Main Street.

Chick and Ruth's | 165 Main Street Annapolis, MD 21401 | 410-269-6737

Think you can handle it? See our challenges below.

3lb Colossal Cheeseburger Food Challenge at Chick and Ruth's Delly
3lb Colossal Cheeseburger Food Challenge at Chick and Ruth's Delly
3lb Colossal Reuben Sandwich Challenge at Chick and Ruth's Delly Annapolis
Customer taking on the 3lb Colossal Burger challenge at Chick and Ruth's Delly in Annapolis.
Winners proudly displaying their official Chick and Ruth's Colossal Food Challenge finisher T-shirts.

The Colossal Sandwich Challenge

Take on the heavyweight champion of Annapolis. This challenge is a 3-pound test of endurance and flavor.

  • The Feat: Finish either our 3 lb. Colossal Reuben (Corned Beef & Pastrami) or our 3 lb. Colossal Cheeseburger.
  • The Rules: One person. 60-minute time limit. You must consume the entire sandwich (including the sides) to be declared the winner. No sharing, no help.
  • The Reward: * An exclusive Chick and Ruth's Challenge T-Shirt.
    • Your victory photo posted to our Social Media Wall of Fame.
    • The pride of conquering a 3lb legend.
Customer participating in the Colossal 6lb Milkshake Challenge at Chick and Ruth's.
Customer participating in the Colossal 6lb Milkshake Challenge at Chick and Ruth's.
Proud winner of the Chick and Ruth's Colossal Food Challenge wearing the official orange finisher T-shirt.
Man attempting the 6lb Milkshake Challenge at Chick and Ruth's Delly in Annapolis.
Group of winners celebrating with 6lb Milkshake Challenge finisher T-shirts at Chick and Ruth's Annapolis.

The Colossal Shake Challenge

96 ounces of pure deliciousness. This is the 6 lb. milkshake that has become a rite of passage for visitors and locals alike.

  • The Feat: Finish a massive 6 lb. Milkshake (Vanilla, Chocolate, or Strawberry).
  • The Rules: One person. 60-minute time limit. Every drop must be finished within the hour to win the prize.
  • The Reward: * An official Chick and Ruth's Challenge T-Shirt.
    • A victory post on our Facebook and Instagram pages.
    • Bragging rights for finishing the most famous shake in Maryland.
Man vs Food Chick and Ruth's Annapolis
Man vs Food Chick and Ruth's Annapolis
The Man v. Food Ultimate Challenge 1.5lb Reuben and 6lb Milkshake at Chick and Ruth's
Man v. Food Challenge winner holding finisher shirt at Chick and Ruth's Delly Annapolis
Proud winner wearing the official black Man v. Food Ultimate Challenge finisher T-shirt at Chick and Ruth's Delly.

The "Man v. Food" Ultimate Challenge

Step into the shoes of Adam Richman. This is the exact gauntlet thrown down on the Travel Channel’s Man v. Food. It combines our two most famous items into one ultimate test.

  • The Feat: Consume a 1.5 lb. Colossal Sandwich (Reuben or Burger) AND the 6 lb. Milkshake.
  • The Rules: One person. 60-minute time limit. You must finish both items entirely within one hour.
  • The Reward: * The exclusive Ultimate Challenge Winner T-Shirt.
    • Keep the large milkshake jar!
    • Your meal is free!
    • Featured placement on our Social Media channels.
    • Membership in the elite club of "Man v. Food" finishers.
Chick and Ruth's Annapolis
Sunday - Thursday
6:30am to 9pm
Friday and Saturday
6:30am to 11pm

© Chick and Ruth's 2026