Chick & Ruth’s Delly in downtown Annapolis has been selected as Maryland’s representative on The Takeout’s list of the “Best Hole-In-The-Wall Spots For Comfort Food In Every State.”
For the list, The Takeout set out to highlight mom-and-pop restaurants across the country known for familiar comfort food, from classic sandwiches and breakfast dishes to casseroles and scratch-made desserts.
For Maryland, the publication selected Chick & Ruth’s Delly, the longtime Main Street landmark that has been serving Annapolis since 1965.
The Takeout highlighted the restaurant’s all-day breakfast, including crab omelets and biscuits with sausage gravy, before pointing to some of its more distinctly Maryland offerings. Those include crab mac and cheese and Annapolis fries topped with crab dip, Old Bay, and cheddar. The publication also praised the deli fare and popular milkshakes.
Located at 165 Main Street in downtown Annapolis, Chick & Ruth’s was founded by Charles “Chick” Levitt and his wife, Ruth, after the couple moved from Baltimore and took over an existing sandwich shop space.
Over the decades, the restaurant became an Annapolis institution known for its New York-style deli sandwiches, breakfast, soups, pies, crab cakes, milkshakes, and deep ties to Maryland politics. Its menu has famously featured dishes named for political figures and local personalities, and every Maryland governor since the restaurant opened has visited.
Chick & Ruth’s has also earned national attention for its oversized food challenges, including enormous sandwiches and six-pound milkshakes. The challenges have been featured on television programs including Travel Channel’s “Man v. Food.”
The Levitt family operated the restaurant for decades, including longtime owner Ted Levitt, the son of Chick and Ruth. Ownership changed hands in 2017, while many of the restaurant’s longtime traditions, menu items, and familiar atmosphere have remained.
