If you walk down Main Street in Annapolis and don't see a line snaking out the door of a bright yellow building, check your watch. You might be there at 3:00 AM. Otherwise, Chick and Ruth's Delly Annapolis is pretty much always humming.
It's loud. It’s cramped. Honestly, it’s a little chaotic.
But that’s exactly why people love it. For over 60 years, this spot has been the unofficial living room of Maryland’s capital. It’s where midshipmen from the Naval Academy rub elbows with state senators, and where tourists try—and usually fail—to finish milkshakes the size of a human head.
The Morning Ritual You Won't Find Anywhere Else
Most restaurants have a morning rush. Chick and Ruth’s has a morning ceremony.
Every weekday at 8:30 AM (and 9:30 AM on weekends), the entire place stops. The grill stops hissing. The waitresses put down the coffee pots. Everyone stands up, faces the flag, and recites the Pledge of Allegiance.
It’s been happening since 1989.
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If you’re a tourist, it’s a bit of a culture shock. One minute you’re debating between a bagel or a Benedict, and the next, you're part of a civic tradition. It started with the original owner, Chick Levitt, and it hasn't skipped a beat under the new leadership of Spencer Jones. Jones, who took over after his father Keith passed away in 2021, is currently running for Anne Arundel County Council in the 2026 election, proving the delly remains a political powerhouse.
Eating the Maryland Government
The menu here is basically a phone book. Seriously, it's massive.
But the quirk is in the names. Almost every sandwich is named after a local politician, judge, or Maryland celebrity. You can literally eat "The Wes Moore" or order a "Hogan’s Hero."
Pro Tip: If you want the quintessential Maryland experience, you go for the crab cakes. They aren't the dainty, filler-heavy cakes you find in tourist traps. These are colossal, jumbo lump masterpieces.
The deli doesn't just do lunch. They are famous for the "Man v. Food" challenges. Remember Adam Richman? He famously tackled the 6-pound milkshake and the 1.5-pound colossal sandwich here. Most mortals shouldn't try this alone. If you do, and you win, you get a shirt and a spot on the "Wall of Fame." If you lose? Welcome to the "Wall of Shame."
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Why It’s More Than Just a Diner
Walking into Chick and Ruth’s feels like stepping into a time capsule that someone keeps adding stickers to. The walls are covered—and I mean covered—in photos of every governor since the 1960s.
There's a specific booth reserved for the Governor of Maryland. The tradition is that the Governor sits on the right side of the booth if they are a Republican and the left side if they are a Democrat. It’s that kind of detail that makes this place feel like the "Cheers" of Annapolis.
What to expect on your first visit:
- Tight Squeezes: The booths are narrow. If you’re a party of six, prepare to get cozy.
- Speedy Service: The staff here doesn't dawdle. They’ve seen it all and they move fast.
- Freshness: They still bake their own bread and pies daily. The smell of the bakery hitting you at the door is half the experience.
The New Era of a Classic
In 2017, the Levitt family sold the business to Keith Jones. There was a lot of local anxiety about that. People worried the soul of the place would vanish. But the Jones family doubled down on the history.
They renovated the Inn on Main (formerly the Scotlaur Inn) located right above the deli. It’s one of the best places to stay if you want to be in the heart of the action. You wake up, walk downstairs, and you're already at the best breakfast spot in town.
Spencer Jones has kept the traditions alive while navigating the complexities of running a legacy business in 2026. The delly is currently celebrating its 60th anniversary, a milestone that few independent restaurants ever see.
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How to Do Chick and Ruth’s Right
If you’re planning a trip, don't just wing it.
First, get there early. If you want to see the Pledge, arrive by 8:15 AM to secure a seat. Second, don't sleep on the breakfast. The Crab Cake Eggs Benedict is often cited as the best in the state for a reason.
Third, check out the bakery counter on your way out. Their black and white cookies are legendary, and the "Whoopie Pies" are massive enough to share.
Actually, share everything. The portions are geared toward hungry midshipmen who just finished a ten-mile run.
Essential Logistics for 2026
- Location: 165 Main Street, Annapolis, MD.
- Hours: Generally 6:30 AM to 10:00 PM (open until 11:00 PM on Fridays and Saturdays).
- Parking: Main Street parking is a nightmare. Use the Hillman Garage nearby; it’s worth the fee to avoid circling for forty minutes.
- Shipping: If you fall in love with the crab cakes, they actually ship them nationwide.
Chick and Ruth's Delly Annapolis isn't trying to be a Michelin-star restaurant. It doesn't want to be "modern" or "sleek." It’s a place that embraces its clutter, its history, and its community. Whether you're there for the politics or the 6-pound shake, you’re part of the story the second you sit down.
To make the most of your visit, plan to walk the waterfront immediately after your meal. You'll need the exercise to work off the "Colossal" sandwich, and the walk from Main Street to the City Dock is the perfect way to soak in the rest of historic Annapolis.