Gilles has been serving frozen custard on the west side of Milwaukee since they opened in 1938—it was the first custard stand in the city. Today, they're still a favorite hangout of local high school students and busy families who want to grab a quick dinner before heading to Hart Park for a football game.
The Gilles' Oreo shake has always been my favorite. They use Oreos that have been finely ground, so there's usually very few chunks that get stuck in the straw. The fine crumbs mix into the custard very well, giving it an overall darker hue and that characteristic chocolate flavor throughout. It's right on the verge of being too thick, but I like to walk that line, even if the straw collapses sometimes. The only drawback to Oreo shakes is that the crumbs result in a somewhat gritty texture.
You can also combine two shake flavors for an extra sixty cents, so I went for the classic peanut butter and fudge. To say that this shake is for peanut butter lovers would be an understatement—there was so much peanut butter that it tasted like you took a drink from a jar of Skippy. The fudge didn't shine through quite enough, but the texture was rich and smooth. I needed a glass of water to wash it down.
Gilles also has a full grill with your standard burgers, fries and dogs, plus a few specialties like a homemade sloppy joe they call the Gilleburger. (See AHT review here.) Even if you go to Gilles for a meal, it's hard to pass up a shake, though you may want to share.