A Little Taste of Summer in These (Brrr) Cold Winter Months

A few weeks ago my friends and I decided we’d had enough of winter.  The thermometer said -2 degrees, but it actually felt much colder.  Something about the winter months make summery things more alluring.  Then, someone said “Let’s make pineapple upside cake.” I thought: “That’s perfect!”.  It’s sweet, with hints of a tropical vacation. Before I knew it we were headed to Wegman’s to search for pineapple and cherries.   Making cute little cupcakes instead of a cake sounded like fun, too. To save time, I adapted a Pillsbury vanilla cake mix recipe for this, so I guess you could say this dessert is semi-homemade.  Honestly, either way you make these treats, they don’t disappoint.

(recipe below)

Once my boyfriend tried these, he ate three and then he tried to steal a few to take back to his place!  He felt obligated since I dubbed him the “official food taster around here”.

Pineapple Upside Down Cupcakes

I wanted these to be super moist and flavorful so I adapted the Pillsbury recipe by adding 1/4 cup of heavy cream, 2 tablespoons of ricotta cheese and a teaspoon of vanilla.  Since this is a super sweet dessert, it could use some toning down to complement the topping of brown sugar, pineapples and cherries, which add a ton of extra sugar. The added teaspoon of vanilla should keep the pineapple from being too overpowering.

Pineapple Upside Down Cupcakes

These eye-catching treats are moist and will satisfy your sweet tooth. Perfect for parties - these treats will have your guests begging for more and asking for the recipe.


  • 1 Small sliced pineapple (canned pineapple works, too)
  • 1 jar 8 - 10 oz. maraschino cherries
  • 1 box cake mix (vanilla)
  • 1 stick unsalted butter
  • 2 tablespoons ricotta cheese
  • 1/2 cup heavy cream
  • 1 teaspoon vanilla
  • 1/2 cup olive oil
  • 1 cup water
  • 2 eggs


Pre-heat oven to the temperature written on the cake box. If you are baking a cake from scratch, pre-heat oven to the temperature I use for cupcakes: 350 degrees.
Prepare a cupcake tin by spraying with non-stick oil or applying with melted butter. I do this by taking a paper towel and dabbing into some room-temperature butter, then rubbing on the insides of the cupcake tin.
Mix water, oil, eggs, ricotta cheese, heavy cream and vanilla with cake mix.
Place a teaspoon of brown sugar in each cupcake section of the tin.
Slice pineapple into tiny pieces and arrange a circle in each cupcake portion in the tin. You can arrange the slices in a circle or any other design you like.
Place a cherry (sliced in half) in each cupcake tin portion.
Pour batter in the tin. Note: Be careful not to over-fill. If the cupcakes are too big, they are more difficult to remove from the pan when they are done baking. I stick to a 3/4 full rule. That is, if you fill up the cups to only 3/4 full, they fall out of the pan much easier after baking!
Place tin in oven and bake for 10 - 15 minutes. Test out if they are done by putting a toothpick or fork in one and if it comes out clean, they are done.
Once cooled (after 15 - 30 minutes), place a large pan over the cupcake tin and flip them over. Gently tap each cup of the tin until the cupcakes fall out onto the large pan. You may have to tap them firmly to get them to come out. Gently lift the cupcake tin and take a peek to see if they've fallen out.