Chick & Ruth Levitt began with a straightforward ethos that remains at the heart of Chick & Ruth's Delly: deliver friendly service and good food. This philosophy has not only lasted over six decades but also has woven Chick & Ruth’s into the very fabric of Annapolis. Known for its scratch-made soups, sandwiches, platters, pies, and the acclaimed crab cakes, the deli has maintained an inviting and down-to-earth atmosphere.

Chick & Ruth’s has also become famous for its Colossal Challenges, a testament to the daring and appetite of its patrons. These gastronomic feats include devouring massive sandwiches, giant milkshakes, and more, all against the clock. Those bold enough to take on the challenges aim for the glory of t-shirts, photos on the wall, and, of course, bragging rights. The inaugural Colossal Challenge involved a 1½ pound sandwich and 6lb milkshake, a spectacle that even drew the attention of the Travel Channel’s 'Man vs. Food' to document the epic endeavor.