The infamous monster size at Polly Ann Ice Cream - a classic city shake
The infamous monster size at Polly Ann Ice Cream, a classic city shake

I’ve been a student of San Francisco shakeology (the science of city milkshakes) for my whole life, but I have noticed an in-town trend towards outrageousness just over the past few years. Many chills, thrills, and bellyaches have been experienced to be your Dairy Queen and bring you this survey of just how crazy it gets out there these days. Shake it up, baby!

 The Twinkie shake at Burger Bar
The Twinkie shake at Burger Bar

High atop Macy’s in Union Square, Hubert Keller’s Burger Bar playfully pokes fun at the American obsession for fast food with incredibly over-the-top versions of staples including a burger with foie gras, fries cooked in high-quality truffle oil, and heart-stopping milkshakes in child and adult (read: alcoholic) form. In the kid column, the craziest item one can order is the Twinkie shake. Rather than a research error, we deliberately did not ask how many of those Hostess bombs are stuffed into the blender with the vanilla ice cream, but we do know that a whole one is cut and thrown in the glass as a garnish — and maybe an extra f*ck you to those nuts enough to try it?

Salted coffee caramel shake at Greenburgers
Salted coffee caramel shake at Greenburger’s

Greenburger’s, which opened in mid-March in the Lower Haight, has a milkshake and sundae bar that you can sidle up to for a sip. Though it hasn’t been around too long, word of its excellent shakes is starting to travel, and we were taken with the salted coffee caramel, made with Strauss vanilla ice cream, French organic coffee, caramel sauce, and fleur de sel. In addition to the salted coffee caramel, vanilla, and chocolate, there is a weekly changing special that tends towards the extra-decadent; recent flavors include carrot cake and bananas foster.

The green chile apple pie shake at Chile Pies and Ice Cream
The green chile apple pie shake at Chile Pies (& Ice Cream)

Chile Pies (& Ice Cream) in the Panhandle offers ice cream by the scoop from Bay Area company Three Twins, but it seems silly to go for a cone when the Green Chile Kitchen offshoot features pie shakes: Milkshakes with a generous slice of house-made pie blended into it. We suspect that there is no pie there that wouldn’t make for an incredible shake (particularly the Mexican chocolate with pecan, hello). However, it’s only proper to opt for the signature pie, an apple studded with green chiles and surrounded with a cheddar-baked crust. A cheese shake doesn’t sound that appetizing on paper, nor does a chile one, but it truly is all a taste combination actually worth experiencing. A spoon is essential to capture chunks of crust too large to blend. I won’t tell anyone that these shakes are about 1000 calories in a glass if you won’t. (There. It never happened.)

Ube and Grasshopper shakes from Mitchells
Ube and Grasshopper shakes from Mitchell’s

Come to think of it, it’s always been easier to get a wild milkshake at city stalwarts Mitchell’s Ice Cream and Polly Ann Ice Cream than to get something relatively plain. Mitchell’s in the Mission is known for its exotic fruit flavors, and the bright purple ube (yam) is certainly the most wonderfully hued shake in town. Mitchell’s offers three suggestions for shakes, and three of them surprisingly contain Oreo cookies. The one to get is the Grasshopper, which blends grasshopper pie ice cream (mint with Oreos), more Oreos, and chocolate syrup. It’s the beverage equivalent of downing a box of Girl Scout Thin Mints in one go.

A Star Wars shake at Polly Ann Ice Cream
A Star Wars shake at Polly Ann Ice Cream

Exotic fruits are also a mainstay at Polly Ann, where it’s difficult to find much in the way of conventional flavors — which is why I’ve loved it since before I was able to walk. I’ve never had the guts to try a shake with durian, the fruit that famously smells like gasoline, but I am curious. I also wonder what it would taste like to make a shake out of Polly Ann’s gummi bear flavor, but that’s perhaps best kept as a mystery for anyone over the age of 10. A shake made with Star Wars (mint ice cream with marshmallows) is a sleeper of outrageousness, especially considering that the ice cream probably starts with the highest fat content in this 7×7 town without the marshmallow assistance. The Sunset mainstay has offered a “monster” size, which clocks in at more than a quart, for more than 30 years. Guess we’ve always been crazy around here.

Milkshake Madness: San Francisco’s Most Outrageous Sips 25 April,2011Tamara Palmer


Tamara Palmer

I’m a freelance writer/editor specializing in food and music, which is truly my dream combination. I’m the editor of The Feast San Francisco, a forthcoming site from NBC, and have written more than 1000 posts for SF Weekly’s SFoodie blog. Music is an equal passion, and encompasses a wide variety of sonic territory. I am the author of the book Country Fried Soul: Adventures in Dirty South Hip-Hop and a co-author of Singles: Six Decades of Hot Hits and Classic Cuts. Whether it’s interviewing Eric Ripert or Stevie Wonder, my job never ceases to bring amazing moments to my life and I’m excited to merge my two great loves into my work for Bay Area Bites.

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