I've now been to The Old Fashioned twice. I know this is a Madison staple and a big deal. I'd hate to say it, but I don't get the craze for it.
$1 Old Fashioneds once a year? Sure, why not.
Full price Old Fashioneds the remainder? I will pass. My wife and I, along with a friend, stopped by and we ordered three different Old Fashioneds. They were "okay." We weren't blown away by the namesake cocktail and they really weren't all that good no matter where they came from.
The menu is creative, but either we had a less skilled bartender or the quality just isn't there.
There are a lot of better bars or or near the square. Try Cask & Ale or Merchant.
Cheers!