Over the weekend, I attended New Windsor Community Day, and afterward, I rode around looking at some of the places I used to hang out. I have talked endlessly on the air about my childhood and teen years growing up in the Newburgh/New Windsor area. Newburgh has a bad reputation, but it was actually a great place to grow up. Some of my fondest memories, believe it or not, center around a diner. Not just any diner--I’m talking about the Vails Gate Diner.

Anybody that grew up around New Windsor in the 1970s is familiar with the Vails Gate Diner. It’s where every night ended. They were open 24 hours and they had great food.

Some big memories from the diner for me?

  • 1

    My mom and Dad caught me smoking cigarettes there while I was with a group of friends. They were at a table across the room and I never even saw them. Luckily, they waited until the next day to confront me.

  • 2

    Then there was the time my Mom encouraged (forced) my sister to go on a date with her friend’s son. They went to the movies, but my sister faked sickness to get out of going to the diner with this guy (loser) and risking embarrassment.

  • 3

    One time my bill came to $6.66. I ordered jello to undo the devilish number.

  • 4

    And there was the time my family went there for Sunday breakfast and we stayed so long that they asked us to leave. But they were very nice about it.

  • 5

    One time we were with my sister and brother in law and my boyfriend at the time ordered tea. The waitress said “lemon or milk?” And he said “both.” And we all kept our mouths shut and watched him put both in and then complain that the milk curdled. We still laugh about that.