This Portland staple was originally founded in 1935 and is heavily sought after for its James Beard-endorsed burger.  Skyline has a 1950s diner feel inside, as well as a large back outdoor patio for nice days. Skyline serves classic milkshake flavors, but also serves such flavors as caramel apple and chocolate-covered cherry, for something off the beaten track. Fuller’s pie shakes, with flavors like fresh banana cream pie and coconut cream pie, are particularly thick, delicious concoctions. If one is really hungry, a giant 30-ounce shake is also available.

From classic milkshakes and 1950s diner comfort foods, blue plate specials included, this St. Johns restaurant takes you back in time. Owner David Liberman uses the Multimixer (the milkshake machine McDonalds magnate Ray Kroc sold door-to-door) to make creamy, flavorful milkshakes. Flavors range from the Chocolate Elvis with peanut butter, bananas, and chocolate ice cream, to classics like vanilla, chocolate, or strawberry, with plenty of vegan options. For an extra 50 cents, any milkshake can be made into a malt. Rockabilly Cafe also offers not-to-be-missed boozy milkshakes, such as the rummy Mexican Cocoa, featuring chocolate ice cream, cinnamon, and a “healthy dose of spiced rum.”

Family-run Dairy Hill Ice Cream originally opened in 2015 and now has three locations throughout the Portland area. Milkshakes come in three sizes, with three pre-set ‘house shakes’ available. If the Extreme Coffee Shake, which includes Kona coffee ice cream and a shot of cold brew, is too much of a caffeine commitment, Dairy Hill Ice Cream offers a shot of cold brew espresso that can be added to any shake for $1. The Black Forest Shake, featuring Bordeaux cherry ice cream and hot fudge, is a lovely blend of chocolate and cherry. 

This brightly painted ice cream shop in the Pearl District makes their ice cream in small batches, but that doesn’t mean the options are limited. Usually more than a dozen flavors are available at a given time, with about 200 flavors on rotation. The smooth and creamy ice creams make for excellent milkshakes, with the option to mix-and-match three flavors. When available, combining Belgian chocolate with coffee crackle in a milkshake is a local favorite.

This Sellwood-Moreland sweets shop recently dove head-first into the world of ice cream, and now has a fully loaded milkshake menu. Flavors range from malt chocolate banana to blueberry Fruity Pebble, plus standards like chocolate, vanilla, and strawberry. Milkshakes come in frosty mugs for ease of sipping.

This iconic Portland ice cream shop needs no introduction. Any of its classic flavors — such as pear and blue cheese or strawberry honey balsamic with black pepper — or its funky monthly flavors can be made into milkshakes. The Chocolate Gooey Brownie, in particular, makes a decadent chocolate delightful milkshake.

This family-friendly, DIY craft studio with elaborate milkshakes opened its Portland location earlier this year. While working on your chosen craft kit (pottery painting, wreath making, etc.), you can also enjoy a massive milkshake, with options like a cookie dough shake topped with a cupcake and a chocolate chip cookie. The coffee milkshake includes a honey bun and a biscotti, while the strawberry cheesecake arrives adorned with a strawberry Pop Tart and shortbread cookie. Plus, all the milkshakes served come in a mason jar customers can take home with them.

Open since 1937, the Jim Dandy Drive-In is a Portland institution and one of Oregon’s oldest drive-ins. The menu is so extensive, it is not published online, and this includes their milkshake menu with more than 100 flavor combinations. The Sticky Fingers milkshake — a mixture of vanilla, peanut butter, and Butterfingers — is usually in high demand.

Located in the Powellhurst-Gilbert neighborhood, Cruiser’s Drive-In is one of those old-fashioned, burgers-and-shakes diners, with a long diner counter and a checkered floor. Cruiser’s focus is on its burgers; however, its milkshakes get rave reviews, with flavors like butterscotch, marshmallow, and hot fudge. Cruiser’s also has a serious line up of candy shakes, including options like Reese’s and Heath.