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

Posted on: October 24th, 2013 by Beth Lennon 10 Comments

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

The National Trust for Historic Preservation works to save America's historic places. Join us today to help protect the places that matter to you.

Beth Lennon

Beth Lennon is the creator of the website RetroRoadmap.com. As "Mod Betty," she delights as the retro travel "hostess with the mostess," scouting out cool vintage places and sharing them with the world.

Pop Culture, Travel

10 Responses

  1. Anna Borg

    October 24, 2013

    I really love the photos on this one! The shot of Ted Levitt is great!
    Makes me miss crabcakes so much.

  2. Jeff Tease

    October 24, 2013

    Very interesting, informative and well written. Mod Betty seems to be a veritable font of information. Please let us read more!

  3. Paul Gurcules

    October 24, 2013

    What a great looking place. It looks warm and welcoming, the kind of place my grandfather might have taken me to when I was a lad; and the kind of place I would love to drop in to now.

    Love the posts by Mod Betty. Please keep them coming!

  4. jason

    October 24, 2013

    Great piece! Adding this place to my travel file…

  5. Candi

    October 24, 2013

    We need to get to that Deli soon. Great article as always. Enjoy all your posts! Keep up the great work. You alway find interesting places for us to visit.

  6. John Beres

    October 24, 2013

    We were in Annapolis for a long weekend this time last year and completely missed this gem of a place! Thank you for this great article, motivates us for a revisit to enjoy this one of a kind restaurant in the heart of town.

  7. lf knowlton

    October 25, 2013

    Delighted to read this article and the photos are great, too!
    I’d love to visit nest time I’m in Annapolis!

  8. Suzanne McG

    October 25, 2013

    This makes me want to go back to visit Annapolis now. I’ve only been there once and really loved it but missed Chick and Ruth’s. Mod Betty really brings it alive. Thank you for this post!

  9. PatD

    October 25, 2013

    This was a delightful article, making the “Delly” most enticing! I plan to make a trip to Annapolis just to check it out.

  10. Janet

    October 29, 2013

    I have always wanted to trip down to Annapolis and this gives me one more reason! Thank You!!!