Follow Along As We Search For Portlands Best Old Fashioned Milkshakes

Dated: August 17 2017

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Follow along as we drink through Portland’s old-fashioned milkshakes in search of our favorites. For this story, that means milkshakes spun with hand-scooped ice cream (or soft serve) in a silver cup, likely served in a frosty soda fountain glass. All the better if you get the extras on the side. No pre-mixed shakes here.

We’ll continue to add to this list as we try them. Stay tuned for our 10 best later this month.

The Oregonian/OregonLive



This Nevada-based burger and milkshake chain opened in the Pearl District’s former P.F. Chang’s space in May. You’ll find over-the-top versions of almost everything here, from a $28 wagyu beef burger with foie gras to a boozy milkshake topped with a whole chocolate cupcake.

1139 N.W. Couch St., 503-616-4321,

Samantha Bakall | The Oregonian/OregonLive


Holstein's Bridgetown birthday cake shake

Go big or go home, right? This $15 boozy behemoth is spun with Tillamook vanilla ice cream, Burnside bourbon and chocolate Black Butte Porter cake crumbs, then poured into a chocolate sauce-lined glass rolled in malted milk frosting and caramelized bacon rice crispies then topped with whipped cream, a porter cupcake and confetti sprinkles. (Still with us?). It’s so thick it’s hard to drink, and maybe you just shouldn’t mix alcohol and dairy. We didn’t eat the cupcake, and we skipped most of the frosting/bacon rim, too, because it was too hard to eat. Stick with the classics here unless you’ve got a spare afternoon to nurse a tummyache.

Samantha Bakall | The Oregonian/OregonLive


Jim Dandy Drive-In

A longstanding, Northeast Sandy drive-in decked out in decades of Portland memorabilia. Come here for the burgers, fries and the impressively long milkshake menu that lets you make your flavor dreams come true.

9626 N.E. Sandy Blvd, 503-253-2126


Jim Dandy's grasshopper shake

Hot take: Milkshakes are best when they’re made with soft serve. And if you share that opinion, this place is for you. With more than 100 (!!!) flavors, Jim Dandy is the Disneyland of Milkshakes. After several minutes of deliberation, we tried the grasshopper, here a chocolate soft serve-based mint milkshake with cookie bits. It’s blended in a paper cup (I get it) and it’s perfect.

Samantha Bakall | The Oregonian/OregonLive

Fairley's Pharmacy

Sit down among the aisles of allergy meds, vitamins and orthotic shoe insoles at this full-service pharmacy. One of only a handful of classic soda fountains left in the Portland area, Fairley’s has been open for more than 100 years. Grab one of the vinyl-topped stools at the linoleum-topped bar and order from the chalkboard menu.

7206 N.E. Sandy Blvd, 503-284-1159,

Samantha Bakall | The Oregonian/OregonLive

Fairely's Pharmacy's vanilla malt

It doesn’t get more old-fashioned than this. Spun on a celeste green milkshake machine with hand-scooped Umpqua ice cream, Fairley’s milkshakes arrive in a chilled glass cup with whipped cream and the extras on the side. We just wished there was a cherry on top.  

Samantha Bakall | The Oregonian/OregonLive

Fat City Cafe

Fat City Cafe is a beloved, longstanding greasy spoon in Multnomah Village. Swing by for a hearty breakfast or lunch, or grab a vinyl stool at the counter and get lost in the hundreds of license plates and signs that line the walls.

7820 S.W. Capitol Highway; 503-245-5457

Samantha Bakall | The Oregonian/OregonLive

Fat City Cafe's chocolate milkshake

Sometimes simple is best. We tried the thick, classic chocolate shake here, served with the metal cup on the side. We took ours to-go, but if you’re drinking there, it’ll arrive in a tall glass cup with whipped cream.  

Samantha Bakall | The Oregonian/OregonLive

Humdinger Drive-In

This 37-year-old, sunny-yellow drive-in serves burgers and more and is run by Susie and Gordon Reimer. The pint-sized stand offers more than 60 milkshake flavors, and you’ll often find Gordon or Susie themselves mixing up a cup for you.

8250 S.W. Barbur Blvd, 503-246-8132

Samantha Bakall | The Oregonian/OregonLive

Humdinger Drive-In's strawberry milkshake

Take a trip down memory lane at Humdinger. While there are more than 60 flavors, we still love the classics. We tried the strawberry, with hand-scooped vanilla ice cream and fresh strawberries blended into a fruity, bubblegum pink shake. We considered a round of tater tots, too, but we’ll save that for our next visit.


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Mark Ross

For Mark Ross, founder of Ross NW Real Estate and professional real estate broker, real estate has always been the career of choice. During his 25+ years in the industry, Mark has gained experience in....

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