Who’s ready for a tropical getaway? *raises both hands and one foot*
Get your vicarious vacation with this Cinnamon Pineapple Upside-Down Cake.
Why is Cinnamon Pineapple Upside-Down Cake the book-inspired recipe for Pineapple Street?
I don’t think anyone’s surprised to see that the book-inspired recipe for Pineapple Street is a Pineapple Upside-Down Cake.
The book’s main characters live in and around “the fruit streets” of Brooklyn, NY, one of which is obviously Pineapple Street. This tropical fruit also has special significance in the book.
You may be surprised by the “cinnamon” part of this recipe, though. That delicious spice isn’t a traditional part of Pineapple Upside-Down Cake.
A few years ago, one of the desserts served at my friend’s Portuguese wedding was slices of grilled pineapple sprinkled with cinnamon.
OMG, they were delicious. Who knew that cinnamon and pineapple paired so well together? (The Portuguese, apparently.)
I came away from that wedding feast with a full belly and a desire to bake something, anything with pineapple and cinnamon together.
Pineapple Upside-Down Cake: an oldie but a goodie
Believe it or not, this blog post marks the first time I’ve ever tried Pineapple Upside-Down Cake. I was born in the early ‘80s, so I feel like I juuuuuust snuck past this popular retro cake that graced so many dinner parties in the ’70s.
While I’ve certainly seen it before – mostly on church tables – I’ve never had an urge to taste it. Nothing about Pineapple Upside-Down Cake ever seemed very appealing, apart from the maraschino cherries that I’d pluck off any slice that was handed to me.
I prefer using fresh fruit in my bakes instead of canned fruit, and Pineapple Upside-Down Cake seems like a nod to the heyday of ultra-processed foods that’s better left in the past.
After one bite, though, I understood why this retro classic has stood the test of time.
What I love about Cinnamon Pineapple Upside-Down Cake
You guys — this Cinnamon Pineapple Upside-Down Cake is pretty damn tasty. I admittedly went a little bougie and bought organic canned pineapple rings and near-to-organic-as-I-could-get maraschino cherries for my bake.
Because, if I’m going to use canned fruit, it might as well be The Best.
Let’s be clear – I’m not a huge pineapple fan. I can take it or leave it, but I mostly prefer to leave it. I fully expected to eat the vanilla cake below and scrape the fruit topping to one side after the requisite sample taste.
But the pineapples covered in this gooey, syrupy cinnamon, vanilla, and brown sugar mixture are Somethin’ Else. I loved them. More than the cake, even!
The pineapple topping caramelizes in the pan as the cake bakes, and I adored the richness of that butter and dark brown sugar mixed with the warm cinnamon. That glaze is what gives the cake its dark color.
And, the pineapple itself bakes down into soft, tender, melting rings that completely loose the acidity they have when raw.
The cake layer itself is a brown sugar vanilla cake with a hint of pineapple flavor in it. Its simplicity is perfect with the sweet caramelly topping.
And, those pecans soaked up the cinnamon sugar mixture and were positively decadent whenever I got one with a bite of cake.
What do you serve with Pineapple Upside-Down Cake?
This retro dessert deserves a retro-inspired meal. Serve Pineapple Upside-Down Cake after a dinner of Chicken and Rice Casserole or One Pot Cheeseburger Mac and Cheese. Pour yourself a tall Shirley Temple Mocktail to wash it all down with.
If you’re looking for other fruity desserts, try Grilled Peaches with Cinnamon and Cream, Strawberry Pie, New England Blackberry Cobbler, and Cherry Pie Bars.
Cinnamon Pecan Pineapple Upside-Down Cake
Ingredients
TOPPING INGREDIENTS
- 4 tbsp unsalted butter
- 1/2 tsp vanilla extract
- 1/2 cup dark brown sugar, firmly packed
- 1 tsp ground cinnamon
- 1 20-oz can of pineapple rings, with juice reserved
- 12-16 maraschino cherries, drained (or more to taste)
- handful of pecan halves (or more to taste)
CAKE INGREDIENTS
- 4 tbsp unsalted butter, at room temperature
- 1/2 cup light brown sugar, firmly packed
- 1/4 cup granulated sugar
- 1 egg, at room temperature
- 1 tsp vanilla extract
- 2 tbsp reserved pineapple juice from the 20-oz can
- 1 1/2 cups all-purpose flour
- 1 3/4 tsp baking powder
- 3/4 tsp salt
- 1/2 cup milk, at room temperature
Instructions
PREP INSTRUCTIONS
- Preheat your oven to 350F.
- Open the can of pineapple rings and remove 2 tbsp of the pineapple juice. Set aside the reserved juice, and you can discard the rest.
- Melt 4 tbsp of butter, then stir in 1/2 tsp vanilla extract. Set aside.
- Stir together the dark brown sugar and 1 tsp ground cinnamon until combined.
- Have a cake plate or cake stand ready for later.
TOPPING INSTRUCTIONS
- Pour the melted butter directly into a 9" round baking pan. DO NOT SPRAY OR LINE THE BOTTOM OF THE PAN.
- Sprinkle the cinnamon sugar mixture all over the melted butter.
- Arrange the pineapple rings in a single layer over the sugar and butter. You can squish the rings together to fit more in the pan; just be sure the rings don't overlap.
- Arrange the maraschino cherries inside and around the rings, then add the pecans around the cherries and pineapple. Again, everything must be in a single layer. Then, set cake pan aside.
BAKING INSTRUCTIONS
- Use a hand-mixer to cream together the 4 tbsp softened butter, granulated sugar, and light brown sugar in a large bowl until light and fluffy.
- Beat in the egg, the 1 tsp vanilla extract, and the reserved pineapple juice until combined.
- In a separate medium bowl, whisk together the flour, baking powder, and salt.
- Alternate adding the dry ingredients and the milk into the butter mixture, beating on low between each addition until ingredients are just combined.
- Carefully pour the cake batter over the arranged pineapple, cherries, and nuts in the cake pan. Smooth batter to the edges of the pan to ensure an even cake layer.
- Bake the Cinnamon Pineapple Upside-Down Cake at 350F for about 40 minutes, or until a toothpick inserted into the middle of the cake comes out clean.
- Remove Cinnamon Pineapple-Upside Down Cake from the oven and let cool in pan on a wire track for ONLY 5 MINUTES.
- Run a knife around the edges of the pan to loosen the sides of the cake.
- Using oven mitts, cover the cake with the bottom of your cake plate/stand. Securely hold the cake plate against the baking pan, then quickly but carefully flip the cake over so that the pineapple "bottom" is now the topping of the cake. Carefully lift the cake pan up and away from the cake. Let Cinnamon Pineapple Upside-Down Cake cool completely before serving.
