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Found another old photo of Cypress in an http://www.middletownpress.com/article/MI/20170208/NEWS/170209675 article from the Middletown Press that covers the restaurant’s history in more detail than I’ve seen elsewhere. This is dated 1941 and shows when they first started to add on to the dining car.
I just meant that I’ve seen lots of older places where the phone was right out in the open, so this booth would have made the call a bit more private. But yeah. Definitely something from restaurants whose heyday was before my time…
Now you’ve got me wondering if the Carta twins would be willing to dig up some historical Cypress menus, so I could see what they were offering decades ago.
My father owned a slaughter house about a mile from the Cypress and I ate there often as a kid. I hadn’t thought of that place in a million years. By the way, that’s not a “privacy booth.” It’s an old telephone booth.
Yeah – they had so thoroughly converted the exterior that the array of windows was the only thing giving away the dining car origins. Almost makes you want to tear off the siding and shingles to see the treasure underneath…
Thanks for the piece Ketteract. I love the fact that it started as an early Dining Car…maybe a Bixler.
Looks like a great old place!

Anonymous
A few weeks ago, I was at a Dunkin’ Donuts on the Berlin Turnpike. I’d only intended to grab my coffee and get out, but then I spotted a couple of comfy chairs, and, sitting on the table next to them, the latest Hartford Courant. It had been several years since I picked up a print newspaper, and I decided, at that moment, to relax and extend my DD visit.
This seized my attention:
(Full version of that article http://www.courant.com/community/middletown/hc-middletown-cypress-restaurant-closing-0204-20170203-story.html here.) I’d never heard of the Cypress Restaurant during the two years that I lived in Middletown – but then, I’d really been on the outer edge of Middletown, and I’d yet to truly develop my habits of food exploration. My mind was turned to http://forums.roadfood.com/Riefe39s-Restaurant-in-the-Quad-Cities-is-closing-m822214.aspx Riefe’s in my hometown of Davenport, Iowa: another long-running comfort food restaurant operated by a single family. They had recently closed after almost 70 years, and I’d made sure to get in one last visit. I resolved to do the same for Cypress despite having no personal connection with the place.
Their Facebook cover photo shows them from earlier times. The original dining car was heavily added onto over the years.
The Courant article shows them as they will be until this coming Monday.
Today was literally my last day to get a proper lunch or dinner out of them, as tomorrow was going to be breakfast only, followed by the farewell party. I headed down from Hartford shortly after they opened at 11 am.
I was immediately charmed.
How many people had sat in these wooden booths? I know it’s a cliche to say that one can “feel the history” of a place, but the sense really was palpable here.
I did not quite dare try the old call-button.
It took me a moment to register what this was: a privacy booth for phone calls!
The presence of seafood and grinders on the http://www.cypressgrill.com/menu.htm menu was a reminder that this was Connecticut, not Iowa; the special was enticing, but I’d come here with a specific purpose, and I already had an idea of what I wanted to order. Cypress belonged to a category of old, dying, now-unfashionable restaurants serving up classic American dishes, and I wanted my meal to reflect that. I wanted to get inside that time-capsule for a while.
I began with some bread, and beef and barley soup.
Riefe’s had been known for their smoked pork chop. I didn’t know if Cypress had a similar signature dish, but it seemed a safe bet to order something with a family member’s name attached to it. I chose “Rosie’s meatloaf” with optional onions and gravy, plus sides of steamed broccoli and mashed potatoes.
I ate slowly, listening to customers chat with the server about the closure and tomorrow’s party, watching the traffic go by on Route 17 as generations had before me, looking around at the wooden seats and walls, tasting flavors of foods that I’d known since childhood, trying to commit as much of the experience as I could to memory. It was, in a way, Americana distilled.
The meatloaf, it sh,21,852045,0,132491,32.210.114.135
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Cypress Restaurant in Middletown, CT – closing after 80 years
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