Roasted Pineapple Milkshakes are the refreshing, indulgent, and easy-to-make icy treat you need this summer.
As I write this post, I wish I had one to sip on. Right. Now.
But I’m out of ice cream. And pineapple. So I guess I’ll just continue writing…
Why are Roasted Pineapple Milkshakes the book-inspired recipe for The Continental Divide?
Hats off to The Continental Divide author Bob Johnson. Without him, I never would have known about the deliciousness that is a pineapple milkshake.
Pineapple milkshakes are served in “A Vigorous, Mostly Happy Couple” which is one of my favorite short stories in the book.
While I’ve been known to enjoy banana milkshakes, I’d never heard of a pineapple milkshake. My eyebrows immediately shot up, and I knew that pineapple milkshakes would be the book-inspired recipe for The Continental Divide.
This cooling, fruity treat seemed perfect for the sweltering summer days that spread over Indiana and affect so many of the characters in the stories.
How do you make a Roasted Pineapple Milkshake?
Like so many delicious desserts, Roasted Pineapple Milkshakes require few but quality ingredients.
- I recommend using fresh pineapple instead of canned. I made life easier on myself and bought pre-cut fresh pineapple chunks from the prepared produce section at my supermarket. Sprinkle the pineapple with brown sugar and ground cinnamon, and you’re ready to roast!
- Not to sound all Ina Garten, but use good quality vanilla ice cream, like Haagen-Dazs or Turkey Hill Simply Natural Homemade Vanilla. You want just the ice cream in this milkshake, not any weird ultra-processed ingredients.
- Whole milk is best for making milkshakes, but you could get away with using 2% milk, too.
Make your milkshake your way
You may notice a trend when you look at the ingredient list for this recipe. Everything’s a “generous” or “heaping” measurement of something.
Making a milkshake isn’t an exact science – at least, I don’t think it is. And that’s because everyone likes their milkshakes differently.
I happen to prefer my milkshakes on the “not-too-thick-not-too-thin” side, while some people think that enjoying a milkshake with anything but a spoon is sacrilege. Meanwhile, others think a shake isn’t a shake unless you’re slurping it through a straw.
My recipe for Roasted Pineapple Milkshakes makes one large milkshake, or two smaller milkshakes. You know, in case you want to share a milkshake with someone special. While sitting on your front porch in matching rocking chairs or something adorable like that.
Do you have to roast the pineapple for a pineapple milkshake?
There are lots of pineapple milkshake recipes out there – but there aren’t many roasted pineapple milkshake recipes. I’m not sure why.
Yes, roasting is an extra step. And I’m sure turning on your oven in the summertime is one of the last things you want to do.
But it is so worth it.
Raw pineapple tends to be a little acidic, and I absolutely loved the gentle sweetness that the roasted pineapple brought to this milkshake. Roasting fruit caramelizes its natural sugars, which is always a good thing when we’re talking desserts.
You don’t have to roast your pineapple. But I seriously recommend it. And, if you really don’t wanna turn on your oven, you could probably get away with cooking the pineapple, brown sugar, and cinnamon on the stove to similar effect.
What I love about Roasted Pineapple Milkshakes
You may remember from my Pineapple Upside Down Cake that I’m not a big pineapple fan. Well, this Roasted Pineapple Milkshake has changed all that.
I am obsessed with this drink. It’s incredibly creamy yet surprisingly refreshing.
While you can serve the milkshakes “straight,” treat yo’self and garnish them with whipped cream and a maraschino cherry for that classic soda shop look. I also like to sprinkle mine with a little grated nutmeg.
What do you serve with Roasted Pineapple Milkshakes?
Sip on a Roasted Pineapple Milkshake after a summer lunch of decadent Lobster Tortellini Pasta Salad or fresh and easy Black Bean Burgers with Peach Guacamole.
Go all in on the pineapple theme for dessert by serving slices of Pineapple Upside Cake while you sip your Roasted Pineapple Milkshake. If you’re looking for a less calorific version of this sweet treat, try making a Pineapple Mint Agua Fresca.

Roasted Pineapple Milkshakes
Ingredients
ROASTED PINEAPPLE MILKSHAKE INGREDIENTS
- generous 1 cup bite-size fresh pineapple chunks
- heaping 2 tbsp packed light brown sugar
- heaping 1/4 tsp ground cinnamon
- 2-3 cups good vanilla ice cream
- 1/4 - 1/2 cup whole milk (more milk = thinner milkshake)
OPTIONAL MILKSHAKE GARNISH INGREDIENTS
- whipped cream
- maraschino cherries
- ground nutmeg
- pineapple cube (roasted or raw)
Instructions
ROASTED PINEAPLE INSTRUCTIONS
- Preheat oven to 425F.
- Spray a medium-sized baking dish with cooking spray.
- Cut pineapple into bite-size chunks. Arrange pineapple in a single layer in the prepared baking dish.
- Sprinkle the pineapple with brown sugar and cinnamon, then stir ingredients together until the pineapple is fully coated.
- Roast the pineapple at 425F for 20-25 minutes, until pineapple has softened and become a little gooey.
ROASTED PINEAPPLE MILKSHAKE INSTRUCTIONS
- Add ¼ cup milk and the roasted pineapple, along with any pineapple drippings from the baking dish, into a blender.
- Cover the blender and pulse the mixture 2-3 times to combine the pineapple and the milk.
- Add 2 cups of vanilla ice cream to the blender. Then cover and pulse 2-3 times to combine all ingredients.
- Check the milkshake consistency with a spoon. Add more milk if you want at thinner milkshake; add more ice cream if you want a thicker milkshake. Pulse a few times after adding more of any ingredient.
- Pour Roasted Pineapple Milkshake into a 15-oz glass (or two smaller glasses) and serve immediately. If desired, garnish with a whipped cream, cherries, nutmeg, and a pineapple chunk.