On many occasions, I've thought, "I wish I'd said that," or, "I wish I'd posted that." But those phrases have usually been followed by, "...but I'm glad SOMEBODY did."

Such was the case when I logged onto Facebook and immediately saw a comment from my friend Evelyn Miller, the proprietor of Windy Hollow Restaurant and the Windy Hollow Biscuit House. And who better than to make the comment in question?

I made a list earlier this year as we are getting close to 60 years (2024) at Windy Hollow. Old Hickory is 100+ years old. Moonlite is about 75, The Country Ham was about 74 when it closed this year, Dipper is 69, Wonder Whip is 68, Windy Hollow is 60, Norman McDonalds is 60, and Briarpatch is “more than 50”. Frailey’s Dari Cream on Highway 81 is from the 1960s. There could be a few more that are 50+. But there aren’t many of us left. Let’s add Gary’s Drive and the Cadillac Drive-In Restaurant (later just Cadillac) - both opened in 1954.

She posted it on the History of Owensboro, KY Facebook page, a private group, and when I saw it, that's when it really did hit me just how many restaurants have been thriving for half a century or better in Owensboro. It makes me wonder how many other Kentucky cities can make such a claim.

So how about a salute to these fine establishments with a round-up of some Tri-State Bucket List visits over the years.

Norman MacDonald's Country Drive-In

The Cadillac

Gary's Drive-In

The Big Dipper


Country Ham

Sadly, this local legend closed in 2023 but not before serving up some amazing deliciousness for nearly three-quarters of a century.

You know what this means, don't you? I have some local icons to add to this list. That's what we call a good problem.

Owensboro Restaurants We Miss the Most

These restaurants are no longer in Owensboro and we them BACK!

Gallery Credit: Dave Spencer

Kentucky Restaurants and Bars Featured on National Television

Kentucky has been well-represented on a number of television series, and not just on Diners, Drive-Ins and Dives. Check out the list:

Gallery Credit: Dave Spencer