Chick & Ruth's Delly Named Top Maryland Comfort Spot

The iconic Annapolis eatery earns recognition as the best hole-in-the-wall destination for comfort food.

Updated on Oct. 29, 2026 in Comfort Food

Screen-print poster illustration of a bowl of macaroni and cheese, evoking the nostalgic tradition of a local comfort food landmark. — Chick & Ruth's Delly in Annapolis has been named Maryland’s premier comfort food destination by The Takeout for its historic local appeal. AI Illustration. Upload story photo >

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The Takeout has officially named Chick & Ruth's Delly as Maryland's premier hole-in-the-wall comfort food restaurant. The historic Annapolis staple was recognized for its dedication to classic, familiar dishes.

Why it matters

The recognition highlights the enduring appeal of traditional, family-run establishments within the local community. It underscores the restaurant's long-standing status as a central gathering place for residents and officials alike.

Located at 165 Main Street, the restaurant is known for signature items including crab omelets and milkshakes that can weigh up to 6 pounds during food challenges.

The players

Chick & Ruth's Delly

This Annapolis restaurant is a historic eatery that has served the local community and state politicians since 1965.

The Takeout

This media organization covers food culture and recently released a list of the best hole-in-the-wall restaurants in each state.

Charles and Ruth Levitt

The founders established the deli as a local staple in 1965 before it grew into a regional landmark.

The details

Founded by Charles and Ruth Levitt, the deli has served locals for decades and notably hosted every Maryland governor since its inception. The establishment gained national exposure through its appearance on the Travel Channel show Man v. Food, highlighting its unique menu of crab mac and cheese and biscuits with sausage gravy.

Chick & Ruth's Delly first opened its doors in 1965.
The restaurant's ownership changed hands in 2017.
The Takeout published its list of top comfort food restaurants on October 29, 2026.

Culture Shift

The recognition reflects a broader cultural trend toward valuing long-standing, independent dining establishments over corporate chains. This shift reinforces the role of mom-and-pop venues as essential anchors for community identity and local history.

Residents and visitors may experience increased patronage at the Main Street location following the high-profile recognition. Diners should plan for potential wait times or crowded conditions during peak hours as more people seek out the award-winning menu items.

The takeaway

Supporting long-running neighborhood establishments preserves the unique culinary heritage of the local community. Visitors can experience the restaurant's history by trying its signature comfort dishes that have defined the deli for over six decades.