What’s the Best Diner in Middletown?


What’s the best Diner in town??   I guess it depends what you’re hungry for.

The appeal of breakfast at any hour is so comforting as is the melty cheese layers of tomorrow’s regret spread across crispy golden fries that are dunked in gravy glory.   Not every place in America has these fantastic places.   I know we didn’t have them in California (even scarier I never met a single person or restaurant there that knew what a meatball parm sandwich was, truly unbelievable but then again they get a lot of sunshine and after awhile it must warp your brain).

Lucky for us in Middletown we have The Colonial Diner at 8 Dolsen Avenue on one side of town and The Americana Diner at 420 Route 211 East on the other side of town.

Best Diner In Town-2The Colonial Diner has been around my whole life same name same location.   So obviously they are doing something right.   They are quite famous for their cheesecake.   It was written up in Town and Country Magazine.  Superman Star Christopher Reed used to stop in to the Colonial for a piece of cheesecake on his way to Ithaca college from NYC.   Possibly he became superman as a result of this super cake???   Well I’d take that as a challenge and order it often just in case.

Now the Colonial has the advantage of being just a hop away from the downtown bar scene this place makes a great 2am meal!   It’s also just down the hill from SUNY Orange.  It serves inexpensive hearty breakfasts with endless cups of Jo.  A Middletown Icon not to be missed.

The Americana Diner has been around a long time too.  It’s got a bustling crowd at all hours of the day.  My kids who have tried French fries all over the place all agree that the Americana has the best.

My kids like dipping eggs ( over easy ) and french fries any hour of the day.  I personally love their Greek dishes amazingly delicious especially the tatziki sauce, I order a cup of that with everything.   They have a selection of homemade soups including Lentil my favorite on Wednesdays, that along with a toasted bagel, maybe even a side of crispy crazy big onion rings makes a fantastic lunch.

Oh man now I’m hungry, this and the cheese cake are forcing me to go get some comfort food.

Do so with the many options at these places.  You can have all the things you’d get at one of the big chain restaurants but with local love and tenderness mixed in.   Give them a chance to get you hooked.

Jennifer Brenner
Big Believer in My City

About Jennifer Livesey

Hyper local Middletown Expert. Award winning real estate agent closing the the largest deal my company has ever had since it started in 1938. Given prestigious recognition by the NYS association of commercial brokers for the "Most Creative Deal" of 2015 for bringing the highest rated medicinal cannabis company to Orange County in an 8.9 million dollar land deal. Recently awarded the 2015 Chairman's Circle Award for outstanding sales.
If you need to know where to find the best slice, how to sign up for soccer club, or when trivia night is I can help, because selling you a home or a business here is only a portion of my job. I'm here to help you fall in love with my cities.


  1. Mary Jane Sorrell. says:

    Jennifer, did you live on Ingallst. and attend Truman Moon School a long time ago?

  2. Jim Sorrell says:

    Nothing like a couple of cheesburgers for an app to kill the time before your “Shrimp Basket” gets to the table. The Colonial also had the added benefit of close to home if your ride took off or you realized getting in the car was a bad idea. The Colonial has my vote.

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