Highland Square Tavern

Love it here. Sometimes it gets weird, but that reflects the neighborhood!

This place is a total neighborhood dive bar. The bar is not in great shape, nor are the furniture and fixtures inside of it — Third time was indeed the charm when I was trying to find a bar stool that didn’t feel like it was going to collapse.
We went on wing night and they were $.50 each, with a minimum order of 12. The wings were STELLAR. Large, well coated with hot sauce, and fresh out of the fryer. I wanted to devour them immediately but the hot wings were too hot (pun!).
The beer was not so fresh — it came out kinda funky, like they hadn’t flushed the tap in a while.
Then there was the DJ. He thought this dive bar was a dance club at midnight on Saturday night; the bass was thumpin’ and the volume was cranked. I could barely hear myself think (and I needed to because we were there to play trivia — pride was on the line). It was not even 9pm on a Tuesday. They had a dance floor, but nobody was on it. Yet, as we drank more, the music improved.
Not the worst experience ever. The wings were awesome. The prices weren’t shabby. I guess you pay for what you get at Highland Tavern.

Butch the owner is a great guy, and family friend. Ok yeah its super divey, but cheap drinks and decent bartenders. Straight down madison, it’s worth checking out. Always good music and good times here