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Center Stage: Pineapple Upside Down Milkshakes with Grandbaby Cakes

Jocelyn Delk Adams is an events and media producer with a passion for baking. She created Grandbaby Cakes, a blog inspired by her grandmother, to display classic desserts and modern trends while showcasing the pastry and sweets field in an accessible way. She hopes to inspire bakers to learn new skills and not feel guilty about dessert. She can be found on Twitter, Facebook, Instagram, Pinterest and Google+.

Milkshakes are a huge favorite of mine. The nostalgic flair they provide is undeniable. Each summer while I was growing up, my family had a weekend ritual that involved golf lessons followed by trips to our favorite ice cream parlor.

The first thing I’d order was a tall, cold milkshake with whatever fruit was in season. I came to adore shakes with peach, strawberry, and of course, pineapple. Because my blog Grandbaby Cakes is all about playing around with traditional flavors and desserts I grew up on, I thought a cool twist to the pineapple flavor would be pineapple upside down cake.

Pineapple upside down cake is definitely one of my favorite desserts ever. It is a classic that never goes out of style. The moist sponge cake topped with brown sugar sweetened pineapple rings is absolute perfection. Sometimes it’s difficult to translate the traditional flavors of a beloved dessert into a modern treat but this milkshake definitely succeeds. This is soooo good, y’all! I seriously would have made one for dinner every single night if I didn’t run out of ice cream.

Using my Hamilton Beach drink mixer, I felt like I was back in that ice cream parlor from childhood. Mixing these milkshakes was a cinch, thanks to that mixer. The results were creamy and delicious.

I started by adding a combination of vanilla ice cream and pineapple sherbet to the mixer.  This was an awesome blend of textures: one creamy and one icy. To further build on the pineapple flavor, I added some crushed pineapple, along with milk and a few spices to kick up the flavor. My favorite addition was the caramel sauce which really punched up the richness in this recipe! It gives it the flavor of caramelized pineapples on top of a beautiful upside down cake.

Finally, I topped that off with fresh whipped cream, crumbles of pound cake, pineapple bits, caramel sauce (and a beautiful cherry if you aren’t allergic to them like me.) You get the perfect taste of a pineapple upside down cake in a creamy, cold and delicious summer drink! This will become your favorite dessert this season, trust me.

Pineapple Upside Down Milkshakes

Yield: Serves 2
Author: Hamilton Beach Test Kitchen


  • 1 cup vanilla ice cream
  • 1/2 cup pineapple sherbet
  • 1/4 cup crushed pineapple
  • 1/2-1 cup milk (1/2 cup if you prefer thick shakes and 1 cup if you like them thinner)
  • pinch of ground cinnamon
  • 1 tablespoon caramel sauce
  • Optional: Garnish with fresh whipped cream, cake crumbles, chopped pineapple, caramel sauce and/or cherries


  1. Add vanilla ice cream, pineapple sherbet, crushed pineapple, milk, ground cinnamon and caramel sauce into the steel mixing cup of your drink mixer and process until smooth and blended to your preference. Add more milk if you prefer milkshakes a bit thinner.
  2. Pour milkshake into two glasses and garnish with toppings of your liking.

The classic style of Hamilton Beach® Drink Mixers takes you back to the days of shakes and malts made with real ice cream, fresh fruit and thick chocolate syrup. Now you can mix these delicious drinks in the comfort of your own home. Mixing versatility is optimized with two speeds—you can also make fluffy batters and beat eggs for omelets—as well as enjoy the convenience of an easy-clean, tilt-up design.

Bring more fun into your kitchen. Mix up amazing milkshakes, malts, and other tasty drinks, made possible by The Original Drink Mixer Company™—Hamilton Beach®.

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  1. I entered a milkshake recipe almost exactly like this in the Below Zero Hero milkshake recips contest about 4 yrs ago and was a top 10 finalist. Very similar recipes.

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