In the 90s I used to eat dinner regularly in the Highland Diner on Highland Avenue (Route 9) in Ossining. I have fond memories of the place. It appeared to be a venerable Ossining institution. The author John Cheever who lived in Ossining in the later part of his life used to hang out there. Cheever died in 1982 before I moved here but the restaurant still had pictures of him.
The restaurant changed hands about 10 (?) years ago. I continued to eat there sometimes but it was never quite the same. It has since operated under several names and owners but apparently (despite what appeared to be considerable expenditure on renovations) has struggled financially. Perhaps because one of the things I liked about the place, that it was rarely crowded, didn't change. Its latest incarnation was as the Olympic Diner but when I went to eat there last Saturday I found it closed. As with Charlie Brown's I had not noticed signs of distress (unlike an earlier incarnation which was open for a couple of weeks in the summer without AC before finally giving up the ghost). There were signs saying it would reopen with new management. Perhaps things will work out better this time. However I suspect the traditional diner business model is not as viable as it used to be and some changes may be needed. Which is always tricky as you may lose the old customers without getting enough new ones.
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