October 24, 2013

[Retro Roadmap] Chick & Ruth's Delly: A Family Affair in Annapolis, Md.

Chick & Ruths Delly Annapolis MD -  Exterior. Credit: Beth Lennon, RetroRoadmap.com
Chick & Ruth’s -- a destination for locals and visitors since 1965

The brick lined sidewalks, roads, and buildings of Annapolis, Maryland radiate the classic colonial charm of a historic waterfront city on the Chesapeake. Neutral colors highlight the architectural details on the many Main Street buildings that are well over one hundred years old.

Maybe that's why the shiny orange sign atop Chick & Ruth's Delly on Main Street is such a cheery change of gears, a shock of color as refreshingly unpretentious as the restaurant itself.

Opened in 1965 by Chick Levitt and his wife Ruth, the restaurant quickly became popular with locals as well as visitors, charmed by the friendliness of the couple and their children who all took turns working at the restaurant. Now almost 50 years later the restaurant is still family run by their son Ted ("Uncle Teddy") and his wife Beth.

Chick & Ruths Delly Annapolis MD - Levitt & Son. Credit: Beth Lennon, RetroRoadmap.com
Chick Levitt’s legacy lives on in the spirit of his son Ted, who runs Chick & Ruth’s.

Spend more than a minute in the bustling yellow and orange restaurant and you'll spot Ted checking in with customers, laughing with regulars, even performing magic tricks to entertain diners waiting for their food.

Chick & Ruths Delly Annapolis MD - Ted Levitt at The Counter. Credit: Beth Lennon, RetroRoadmap.com
Ted Levitt in the middle of the action, seated at one of the ringside counter seats

While the original sandwich shop has expanded over the years, it still includes five of the original 10 lunch counter seats. Ted promises to "keep 'em forever" as they are popular with single diners who want to be in the middle of all of the action. And there's action a-plenty at Chick & Ruth's Delly, with wait staff and customers tangoing through the aisle that runs the length of the restaurant.

Chick & Ruths Delly Annapolis MD - Vintage Signs. Credit: Beth Lennon, RetroRoadmap.com
Original hand-lettered signs add to the vintage authenticity of Chick & Ruth’s.

More than a deli, Chick & Ruth's Delly is a neighborhood breakfast/lunch/dinner/late-night destination for the hungry. And hungry you better be, as they pride themselves on signature colossal meals, including half-pound crabcakes. But there's plenty of traditional counter style comfort food available as well, including their extensive menu of sandwiches named after local Maryland political figures.

Chick & Ruths Delly Annapolis MD - Famous Sandwich Menu. Credit: Beth Lennon, RetroRoadmap.com
With Annapolis as the state capital and county seat, there’s always a politician to name a sandwich after.

While the oversized milkshakes (six pounds!) and food challenges may bring in the fans of TV shows like Man vs. Food, and their politically inspired sandwich menu may intrigue the curious, the heart of Chick & Ruth's Delly is more than mere gimmickry for many.

These are the folks that were brought there as children now bring their own children in. Navy vets introduced to the Delly when attending the Naval Academy who return year after year with more stripes on their uniforms. Out-of-towners and locals who make a point to get there early in the morning to recite the Pledge of Allegiance.

Chick & Ruths Delly Annapolis MD - Chick and Ruth Portrait. Credit: Beth Lennon, RetroRoadmap.com
Chick and Ruth overseeing their family-run legacy from above

And more than one couple has honored Chick & Ruth's as the place where they've gotten engaged to be married, perhaps inspired by the union of Chick and Ruth, and their family’s long-running dedication to their classic lunch counter.

Visit Chick & Ruth’s Delly

Chick & Ruth's Delly
165 Main Street
Annapolis, MD 21401
(410) 269-6737

Double the impact of your gift. Help tell the story of America by preserving places that matter and have your year end gift matched!

Donate Today