Follow along as we search for Portland’s best old-fashioned milkshakes
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.
Holstein’s
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, holsteinsburgers.com
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.
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.
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, fairleyspharmacy.com
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.
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
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.
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
