This Maryland Deli Is Famous for Sandwiches Stacked Higher Than Your Appetite

Some sandwiches are snacks. This one is a challenge.

Maryland has a deli famous for piling meat so high you might need a strategy just to take a bite. Pastrami, corned beef, turkey, stacked like a dare between two slices of bread.

The pickles on the side are crunchy, the mustard is zesty, and the whole experience is pure deli magic. Locals have been coming here for years, ordering the same thing and leaving satisfied every time.

Tourists find it and stare in disbelief when the plate arrives. Portions are generous, the atmosphere is lively, and the staff keeps things moving.

That is the mark of a legendary Maryland deli. Sandwiches so big they laugh at your appetite and make you come back for more.

A Living Piece of Annapolis History

Sixty years is a long time for any restaurant to survive, and Chick and Ruth’s Delly has not just survived. It has become the kind of place that people plan their Annapolis trips around.

Founded in August 1965 by Chick and Ruth Levitt, the delly started as a straightforward family operation with a simple goal: feed people well and treat them right.

That original spirit has never really left. The walls are covered in memorabilia, political photos, and decades worth of character that no interior designer could replicate.

Every corner of the place feels earned rather than curated, and that distinction matters more than most people realize when they walk through the door.

Ownership eventually passed to the Levitts’ son Ted and his wife Beth before being sold in 2017 to Keith Jones, a former regular customer who made a public promise to keep the traditions alive. His son Spencer now serves as president of the operation.

The fact that someone bought this place specifically because they loved it as a customer says something genuinely rare about what kind of institution it is. August 2025 marked the delly’s 60th anniversary, and the celebrations felt entirely deserved.

Few restaurants anywhere in Maryland carry this kind of authentic, unforced history, and fewer still manage to stay this relevant across six full decades of changing tastes and trends.

The Sandwiches That Started the Legend

The menu at Chick and Ruth’s runs over 120 items, but the sandwiches are the undisputed stars of the show. Corned beef, pastrami, turkey clubs, and the legendary Reuben are all stacked with portions that feel almost confrontational in the best possible way.

One regular has described the Reuben as so large she stretches it across three separate meals, and that tracks completely.

The bread is baked fresh every single day, including rolls and Kaiser rolls made from scratch in-house. That detail matters more than it might seem, because a sandwich this tall needs a foundation that can actually hold up.

Biting into one of these and having everything stay together is its own small miracle of deli engineering.

Beyond the classics, the Jumbo Lump Crab Cake Sandwich has developed a serious following of its own. Customers consistently describe it as massive and loaded with real crab, which is exactly the kind of review that makes you want to order it immediately.

The half-pound crab cakes are popular enough that the delly ships them nationwide, which tells you they are the real deal and not just a tourist novelty.

More than 120 sandwiches and dishes on the menu are named after elected officials, a tradition that began with Maryland governors and has grown into a genuinely charming piece of local political culture that keeps the menu feeling alive and rooted in the community around it.

The Colossal Challenge That Gets People Talking

Not every deli has a food challenge serious enough to make people genuinely nervous, but Chick and Ruth’s has built an entire reputation around theirs. The Super Colossal Sandwich Challenge involves finishing a three-pound stack of deli meat piled onto a regular-sized bun, all within a one-hour time limit.

That contrast between the enormous filling and the standard bun is both hilarious and deeply intimidating.

Then there is the Man vs. Food Challenge, which pairs a 1.5-pound sandwich with a six-pound milkshake. The milkshake alone is the kind of thing that makes you reconsider your life choices in the most entertaining way possible.

These challenges are not just gimmicks either. They draw real competitors, curious onlookers, and plenty of people who simply want to watch someone attempt the impossible over lunch.

The atmosphere during a challenge attempt is genuinely electric in a way that feels organic rather than staged. Other diners lean in, staff keep a friendly eye on the clock, and there is a kind of collective rooting energy that fills the room.

Whether someone finishes or not almost becomes secondary to the shared experience of watching it unfold. It is the sort of spontaneous entertainment that a place like this generates naturally, without any need for promotion or theatrics.

The challenges have helped put Chick and Ruth’s on the national radar, but the regulars who come in for a quiet Tuesday breakfast are just as much a part of the story.

Morning Rituals That Feel Genuinely American

Every morning at 8:30 on weekdays and 9:30 on weekends, something happens at Chick and Ruth’s that you will not find at any other deli in the country. The Pledge of Allegiance is recited out loud, together, by everyone in the building.

Customers mid-bite, servers mid-pour, cooks mid-flip. All of it pauses for about thirty seconds of collective ritual that has been happening without interruption since 1989.

The first time it happens around you, the effect is genuinely surprising. There is no announcement, no fanfare, just a natural pause and then voices joining in from every corner of the room.

By the time it is over, strangers are smiling at each other in that rare, unguarded way that almost never happens in public anymore.

This tradition was established by the Levitt family and has continued through every ownership change, which says a great deal about how seriously the current team takes the culture of the place. It is not performative or politically charged.

It is simply a daily reminder that this particular restaurant exists inside a community with a shared identity. For visitors who stumble into it without knowing, it becomes one of those travel moments you end up telling people about for years.

For regulars, it is just Tuesday morning. That gap between those two experiences is exactly what makes the tradition so quietly powerful and worth experiencing at least once in person.

The Governor’s Booth and Political Tradition

There is one booth at Chick and Ruth’s that carries more political weight than most conference rooms in Annapolis.

Every Maryland governor since Marvin Mandel has made the trip to eat breakfast at the designated Governor’s Booth on inauguration day, and that tradition has held steady across decades of changing administrations and political climates.

The walls surrounding that booth, and honestly most walls in the restaurant, are covered in signed photos, newspaper clippings, and mementos from politicians, celebrities, and regulars who have passed through over the years.

It gives the whole room a kind of unofficial archive quality that history buffs and casual visitors both tend to appreciate.

You can spend a good ten minutes just reading what is on the walls before your food even arrives.

More than 120 menu items are named after elected officials, a tradition that started with Maryland governors and expanded outward from there.

Ordering a sandwich named after a sitting senator or a former governor is a small, fun way to feel connected to the local political landscape without taking any of it too seriously.

The delly has never positioned itself as a political space, but politics has clearly found it comfortable enough to keep showing up.

That kind of organic relationship between a neighborhood restaurant and the public figures who represent that neighborhood is increasingly rare, and it adds a layer of genuine texture to what might otherwise just be a really good lunch.

Breakfast Worth Waking Up Early For

The breakfast menu at Chick and Ruth’s is the kind of thing that makes you genuinely reconsider sleeping in. Opening daily at 6:30 AM, the delly pulls in early risers, local workers, and visitors who have learned that getting there before the crowd is always worth it.

The portions at breakfast are consistent with the rest of the menu, meaning generous in a way that feels almost personally caring.

House-baked bread and fresh Kaiser rolls show up at the table still carrying warmth from the oven, and that alone sets the tone for everything that follows. The homemade donuts and apple fritters are the kind of thing regulars quietly plan their mornings around without ever really admitting it.

They are not fancy, but they are made with a consistency that is genuinely hard to find.

Hearty comfort food is the throughline of every breakfast plate, from classic egg dishes to thick slices of toast that hold up to whatever you pile on them. The house-made soups, available later in the day, carry that same made-from-scratch energy that makes the food feel grounded and real rather than assembled.

There is something deeply satisfying about eating at a place where the kitchen clearly starts from scratch every single morning rather than opening packages. Breakfast here does not try to be trendy or Instagram-optimized.

It just tries to be good, and it succeeds at that in the most straightforward and honest way possible.

The Atmosphere That Keeps People Coming Back

Some restaurants make you feel like a customer. Chick and Ruth’s makes you feel like a regular, even on your first visit.

The energy inside is warm and slightly chaotic in the best possible way, the kind of controlled bustle that signals a kitchen firing on all cylinders and a front-of-house staff that genuinely knows what they are doing.

The space itself is unpretentious to its core. Booths are worn in rather than worn out, the lighting is comfortable rather than atmospheric, and the noise level hovers at that perfect diner pitch where conversations feel private even in a packed room.

It is the kind of place where families, solo travelers, city workers, and first-time visitors all somehow feel equally at home without anyone having to try too hard.

Friendly service has been part of the delly’s identity from the beginning, and that reputation has held through every ownership transition and every shift in the surrounding neighborhood.

The staff moves with the kind of practiced ease that only comes from genuinely liking where they work, which is something you can feel without being able to fully explain it.

College students from the Naval Academy area mix with longtime Annapolis families and curious tourists, and somehow the whole mix works. There is no dress code, no pretension, and no sense that anyone is being evaluated.

The atmosphere is the point as much as the food, and both deliver in a way that makes you want to come back before you have even finished your first visit.

Planning Your Visit to a True Maryland Original

Getting to Chick and Ruth’s is straightforward since the delly sits right on Main Street in the heart of downtown Annapolis, one of the most walkable and historically rich small cities on the East Coast.

The location makes it an easy addition to any Annapolis itinerary, whether you are there for the waterfront, the Naval Academy, or just a day trip from the DC or Baltimore area.

Hours run Sunday through Thursday from 6:30 AM to 9:00 PM, and Friday through Saturday from 6:30 AM to 11:00 PM, which means there is almost always a good window to fit it into your schedule.

Weekday mornings tend to be a bit calmer, but the weekend energy has its own appeal if you do not mind a little wait.

Arriving early is never a bad idea regardless of when you go.

If you cannot make the trip in person, the half-pound crab cakes are available for nationwide shipping, which is a genuinely solid consolation.

But the full experience, the food challenge energy, the Pledge of Allegiance, the Governor’s Booth, the walls covered in decades of history, really does require showing up in person.

There is no digital version of sitting in that room and having a server drop a sandwich in front of you that is taller than your coffee cup. Some things just have to be experienced directly, and Chick and Ruth’s Delly is absolutely one of them.

Address: 165 Main St, Annapolis, MD