Chick & Ruth’s Delly

Only about a 52-minute drive from Loyola (depending on a slight bit of traffic) is the quaint but vibrant city of Annapolis, Maryland. It’s known for being home to the United States Naval Academy, but the city itself offers so many shops, restaurants, and historic landmarks. There are brick sidewalks, waterfront views, and local spots that feel like they’ve been around forever. One of those places is Chick & Ruth’s Delly.

Chick & Ruth’s has been around since 1965. It was opened by a husband and wife, Chick and Ruth Levitt, and has always been a family-run place. Over the years, it’s become an Annapolis staple that brings people in from all over. They’re known for their food, but also for how much personality the place has. Every morning they say the Pledge of Allegiance, and the walls are covered with photos of politicians, celebrities, and all kinds of regulars who have been coming there for years.

The day started with an easy drive and me picking up my boyfriend Graydon from “Gate 1” of the Naval Academy. The first few times I even drove or rode on base, I was uneasy. They have armed guards, and I had been specifically told that you absolutely must stop at the line and stop sign before the checkpoint and wait for them to wave you up. If you don’t stop, they’ll draw their guns. Safe to say, I clung to that advice and came to a complete stop every single time. Once I was waved through, I parked and waited for Graydon to walk over.

We headed toward downtown Annapolis for a Sunday lunch, walking through the main strip. The sidewalks were packed with people. There were plebes in uniform, older couples strolling slowly, younger families pushing strollers. It is definitely a more put-together crowd, but it's cool because the city has so much to offer for anyone who's living or visiting there.

Chick & Ruth’s looks like your typical diner from the outside, but once you step through the old rickety door (and duck under the clear plastic curtain strips hanging at the entrance), it hits you just how tight and colorful the place is. The space is packed. The walls are completely covered with photos of famous visitors, handwritten notes signed dollar bills, and newspaper clippings filling every inch. I don’t think I saw a single patch of plain wall anywhere.

The staff had this warm, motherly energy. You could tell they had probably worked there forever and had seen it all. We climbed the narrow staircase, each step feeling smaller than the last, and found a table upstairs. We decided to split two things off the menu, but the one non-negotiable? The milkshakes. I had been told they were a must. We each place an order for our own respectable cookies and cream shakes.

Chick & Ruth’s is famous for their Colossal Challenges. There are four in total, including one involving a six-pound milkshake that has to be finished in an hour. This challenge even showed up on Man v. Food, which was a favorite of mine and my two older brothers growing up. On the show, he had to finish a 116-ounce milkshake and a one-and-a-half-pound sandwich. Insane. Not that this appearance put this place on the map, but it has definitely drawn in fans of the show, including some famous people!

As we sat down, the table next to us caught my attention. A girl with ginger hair, probably in her early twenties, sat in the corner booth, holding a massive glass of strawberry milkshake in both hands. Then, over the deli loudspeaker, a voice rang out:

“Hello, Chick and Ruth’s customers! Today we have a new challenger, Sam, attempting the Colossal Challenge!”

Cheering erupted throughout the deli.

“She has exactly one hour to take down the entire six-pound milkshake. Wish her luck!”

More cheers followed.

Graydon turned to me and casually said, “I actually did the challenge freshman year with the cookies and cream one.”

I stared at him. “No way. Did you finish it?”

He nodded like it was no big deal.

He pulled up a picture from his plebe year, still in uniform since plebes have to wear it pretty much all the time, sipping from the massive milkshake. I needed that picture immediately (and got it but wasn't allowed to share unfortunately). 

While we waited for our food, I looked around and saw how many different types of people were there. Some looked like regulars, some were tourists taking pictures of the walls, and a few tables downstairs had midshipmen still in uniform. It kind of reminded me of Baltimore, where you walk into a place and it's just a mix of everyone doing their own thing. It didn’t feel like just a restaurant. It felt more like a local hangout.

Annapolis and Baltimore are very different, but Chick & Ruth’s had that homey, reliable, intimate feel that I think a lot of people would appreciate. There’s so much to take in while eating at a place like this, and something about sitting there makes you want to soak it all in. Especially the stories and the people who’ve been there before you. Since the Naval Academy is a short walk away, it’s brought in plenty of famous visitors like past presidents, athletes, and political figures. It’s cool to see that nobody is “too good” for a little dive-type place like Chick & Ruth’s.

What stood out most wasn’t just the food or the milkshake challenge. It was the feeling of being in a space where everyone felt welcome. Chick & Ruth’s doesn’t try to be fancy or trendy. It is unapologetically itself. It made me think about how food culture in Maryland really brings people together. Whether it's crab houses in Baltimore or a deli like this in Annapolis, these spaces create a shared experience. 

After we finished eating (and sadly but thankfully did not attempt any challenges ourselves), we were on our way. The streets were still busy. I left full from our milkshakes, pizza bagels, and cheesesteak, and already thinking about what I’d order next time.

If you ever find yourself in Annapolis, go to Chick & Ruth’s. Order the milkshake. Take it all in. You’ll leave with a full and happy stomach.