Orlando Magazine

Famous Orlando Diner Kappy’s Subs Will Close Permanently This Week

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The interior of Kappy’s Subs remains mostly unchanged since it’s opening. Photo by Roberto Gonzalez

Kappy’s Subs

Maitland | Established 1967 

This beloved institution is set to close permanently on Saturday, September 14, 2024 or until they sell out. This decision was not their choice, according to a long message on their Facebook page:

“We regret to inform everyone that we will be closing permanently on Saturday, September 14th at 4 pm. Unfortunately, after great effort, we were unable to get to terms with the party acquiring the location. It has been an absolute honor for me and my family to serve this community for the past 52 years. We deeply appreciate everyone who has walked through our doors throughout our time in service and will miss being able to feed y’all every day. Closing Kappy’s is the hardest thing I’ve ever had to do in my life and i have been brought to tears on several occasions in the past few days. Believe me, this is not how we want to go out and is as sudden a surprise to us as it is to everyone else.”

You can’t miss the big Kappy’s sign on Orlando Avenue in Maitland. The no-frills restaurant has been a staple since 1967. “We call ourselves a Maitland tradition,” says owner Rachel Milsom. “There are many families whose kids grew up going to Kappy’s; some met their husbands and wives here or rode their bicycles when in middle school.”

(ROBERTO GONZALEZ)

This unpretentious diner has been in the same family since its opening. It operates out of an original Valentine Diner, essentially an L-shaped box with just 12 swiveling bar stools with weathered cushions, overlooking the kitchen where a calm and collected staff sweats through order after order of burgers, strawberry milkshakes, and Philly cheesesteaks. Valentine Diners were prefab trailers designed to be run by just a few people, and while they’re not being made anymore, the utilitarian charm makes you wonder why they couldn’t make a resurgence someday. The youngest generation of the Caplan family has recently added their own flair to the family business, including a trendy food truck and some innovative additions to the menu. Still, the real magic is simply being able to sit in the roadside dining room of this Maitland-based icon and watch the world drive by on 17-92. 

Under a canopy, folks order at the window and grab a seat at a picnic table out front. Inside there’s a diner-style counter with 12 faded red vinyl stools. Kappy’s is known for its cheesesteak sandwiches—brown beef with American cheese and the traditional Philly. Everything here is handmade from scratch, including favorites like chili, and roast pork, from Kappy’s special recipe, for its Cubans. But what surprises customers are the milkshakes. “We don’t use mixes. We make hand-dipped real ice cream milkshakes. That’s something you just don’t find anymore,” says Milsom. | kappyssubsfl.com

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