Desserts

Bourbon Old Fashioned Upside Down Cake with Winter Oranges

Overhead shot of cut glazed upside down cake in the sheet pan surrounded by a metal cake spatula, two orange halves, three slices of cake, an orange bitters bottle, an Angostura Bitters bottle, and two Old Fashioneds in rocks glasses.
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This Bourbon Old Fashioned Upside Down Cake with Winter Oranges is a moist vanilla buttermilk cake that’s drenched in a hot orange and bourbon butter sauce, making it taste like an Old Fashioned. Eating it while sipping on an Old Fashioned is one of life’s true blissful moments. 

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Overhead close up of a square slice of orange upside down cake.

I’ve not been too fond of sugar lately and really enjoyed my January refined sugar-free month. I allowed myself to use honey, maple syrup, and in some cases, coconut sugar but I tried to not rely on sweeteners in general.

But baking ideas get stuck in my head a lot and refuse to rest until explored. And then there’re food holidays like Valentine’s Day and seasonal produce like oranges. Which is why, despite me not wanting to eat sweets, I went on a baking spree that included an Orange Chess Pie, a Horchata Latte Cheesecake, and this Bourbon Old Fashioned Upside Down Cake.

Vertical side shot of a slice of orange chess pie with the tip gone and a fork stuck in it standing up vertically.
Orange Chess Pie
Overhead shot of cheesecake arranged in a fan shape with one slice laying on its side.
Horchata Latte Cheesecake

The Bourbon Old Fashioned Upside Down Cake got a lot of responses on my Instagram stories so I’m saving the Orange Chess Pie for a rainy day.

Turning a Kentucky Butter Cake into a Bourbon Old Fashioned Upside Down Cake

Overhead shot of uncut upside down cake still in the sheet pan surrounded by three orange halves, an orange bitters bottle, an Angostura Bitters bottle, and two Old Fashioneds in rocks glasses.

I always had a Kentucky Butter Cake at my Grandma’s. It’s usually baked in an angel food cake tube pan or a bundt pan. Apparently, it’s a recipe that was created by Nell Lewis for a Pillsbury Bake-Off Contest in Platte City, Missouri in 1963. And it won. Because it’s the best.

Side view close up of a slice of upside down cake.
Close up overhead shot of the unglazed oranges on the upside down cake.

Even before you pour the hot butter sauce over it, the cake is moist and flavorful. But once you add that sauce, it’s game over. You might as well accept you’re going to have at least two slices.

Overhead close up shot of the oranges on an upside down cake.

When my orange tree kept producing buckets of oranges, the Kentucky Butter Cake is what popped into my mind as being the perfect cake for baking an orange upside down cake.

Overhead shot of raw orange slices laid out in a cake sheet pan.
Close up overhead shot of the unglazed oranges on the upside down cake.

Kentucky Butter Cake was always served with a hot butter sauce in our home. We would poke holes in the hot cake and drizzle the sauce all over it. Which makes this cake an upside-down cake AND a poke cake. And that’s a win in my book.

Side view close up of the edge of a slice of upside down cake.

It’s the sauce that got me thinking of making this an Old Fashioned themed upside down cake. I replaced the water in the sauce with a 50/50 mix of fresh squeezed orange juice and bourbon. Once the butter is completely melted and the sugar dissolved, a couple dashes of orange bitters and Angostura Bitters really make it into an Old Fashioned Hot Butter Sauce.

Close up overhead shot of the unglazed oranges on the upside down cake.

I knew I had gotten it right when one of my sisters tried it and told me, “I don’t know if this is supposed to go with an Old Fashioned, but it would go great with one.”

Overhead shot of an Old Fashioned in a rocks glass with a strip of orange and a large square ice cube on a wooden surface.

It’s Always Harder Than You Think

Don’t worry, the cake is really easy to make. But starting a part-time job and trying to blog at the same time is harder than I thought it would be. Which is always how life goes.

I work Monday 8 to 3 and Tuesday, Thursday, and Friday 11 to 6. There’s been some overtime work as well and a lot of things I planned on getting done aren’t done yet.

I’m seriously learning SO MUCH. Sometimes I feel like my brain will explode but I love it. Every week I’ll probably get a little better at fitting in blogging more regularly. In the meantime, just enjoy this Bourbon Old Fashioned Upside Down Cake. And a strong Old Fashioned.

Side view close up of a slice of upside down cake.
Overhead shot of cut glazed upside down cake in the sheet pan surrounded by a metal cake spatula, two orange halves, three slices of cake, an orange bitters bottle, an Angostura Bitters bottle, and two Old Fashioneds in rocks glasses.
5 from 1 vote
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Bourbon Old Fashioned Upside Down Cake with Winter Oranges

This Bourbon Old Fashioned Upside Down Cake with Winter Oranges is a moist vanilla buttermilk cake that’s drenched in a hot orange and bourbon butter sauce that tastes like an Old Fashioned. 
Course Desserts
Servings 15
Author Megan Wells

Ingredients

Upside Down Cake

  • 1/4 cup unsalted butter, melted
  • 1 cup brown sugar
  • 2 tablespoons bourbon
  • 4 to 5 oranges, peeled and thinly sliced*
  • 3 cups flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1 teaspoon salt
  • 1 cup salted butter
  • 2 cups sugar
  • 4 eggs
  • 2 teaspoons vanilla extract
  • 1 cup buttermilk

Old Fashioned Hot Butter Sauce

  • 1/2 cup salted butter
  • 1 cup sugar
  • 1/4 cup bourbon
  • 1/4 cup freshly squeezed orange juice
  • 1/2 teaspoon orange zest
  • 2 dashes orange bitters
  • 2 dashes Angostura Bitters

Instructions

Upside Down Cake

  1. Preheat the oven to 350 degrees Fahrenheit. Grease a 9×13 inch baking pan. 

  2. Melt the butter and pour it into the pan, spreading it out evenly across the surface. 

  3. Sprinkle the brown sugar over the melted butter and pat it down. 

  4. Drizzle the bourbon onto the brown sugar and tilt the pan to spread it around. Pat down and redistribute the brown sugar evenly if it moved. 

  5. Lay the orange slices evenly across the surface and set aside.

  6. Sift together the flour, baking powder, baking soda, and salt into a medium bowl. 

  7. Cream the butter and sugar together until smooth. 

  8. Add the eggs one at a time until just combined. 

  9. Mix the vanilla extract in. 

  10. Alternate adding the buttermilk and the flour mixture until everything is combined. 

  11. Pour and scoop the batter over the orange slices and spread evenly. 

  12. Bake for 50 to 55 minutes or until the cake is done and a toothpick inserted in the center comes out clean. 

  13. Run a knife around the sides of the pan. Place a heatproof serving plate upside down onto the pan and turn the plate and pan over.  

  14. Leave alone for 5 minutes and then remove the pan. Make the Old Fashioned Hot Butter Sauce while waiting. 

  15. Use a fork to poke holes in the cake. Don’t worry about ruining how the cake looks, you don’t notice the holes. Pour the Old Fashioned Hot Butter Sauce over the cake and serve.

Old Fashioned Hot Butter Sauce

  1. Combine the butter, sugar, bourbon, freshly squeezed orange juice, and orange zest in a small saucepan. Cook on medium heat until the butter is melted and the sugar is completely dissolved. Add a couple of dashes of the orange bitters and Angostura Bitters. Pour over the cake. 

Recipe Notes

  • Before peeling the oranges, make sure you zest one to get a 1/2 teaspoon orange zest for the Old Fashioned Hot Butter Sauce. 
  • Get 6 oranges for the whole recipe to be on the safe side. The size of the oranges and how many slices you can get from each will determine how many oranges you will need. The oranges from my tree are big but they’re navel oranges, and the little baby orange inside makes it hard to get very many slices.
  • Also, consider that you need 1/4 cup freshly squeezed orange juice. I got that much juice from half an orange.

Oh and I can’t forget:

OLD FASHIONED RECIPE:

  • 1 rocks glass
  • 1 large ice cube 
  • 2 ounces bourbon
  • 0.5 ounces gum syrup (or regular simple syrup if you can’t find gum syrup)
  • orange bitters
  • Angostura bitters 
  • 1 large orange peel

Place a large ice cube in a rocks glass. Pour the bourbon and gum syrup in and stir for about 10 seconds.

Add a couple of dashes of orange and Angostura bitters.

Use a vegetable peeler to peel off a strip of orange. Twist it over the rocks glass and drop it in. Stir for 15 seconds and serve. 

This Bourbon Old Fashioned Upside Down Cake with Winter Oranges is a moist vanilla buttermilk cake that’s drenched in a hot orange and bourbon butter sauce that tastes like an Old Fashioned. #kentuckybuttercake #pokecake #dessert #bourbon #oldfashioned #oranges | www.megiswell.com

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This Bourbon Old Fashioned Upside Down Cake with Winter Oranges is a moist vanilla buttermilk cake that’s drenched in a hot orange and bourbon butter sauce that tastes like an Old Fashioned. #kentuckybuttercake #pokecake #dessert #bourbon #oldfashioned #oranges | www.megiswell.com

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  1. I think it is JUST WRONG that I’ve never had a KY Butter Cake OR this cake! I need to fix that ASAP- and I hope your new job is going well!!!

    Reply

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  • The second infused sugar I'll be using in the #diyginbar is this Orange Sugar with Szechuan Peppers, which has a bright orange flavor with slight lemony overtones that is simply effervescent.⠀ ⠀ Click on the link in my profile @megiswell to print the recipe or hit save to come back to it later!⠀ ⠀ Ingredients⠀ 2 cups roasted sugar (optional)⠀ 1 teaspoon Szechuan peppers⠀ 1 tablespoon orange zest⠀ ⠀ Instructions⠀ Preheat oven to 325 degrees. Pour 2 cups of refined white sugar into a 6×10-inch glass baking dish and roast for 2 hours, stirring every 10 minutes. It should be a sandy tan color and coarse, like turbinado sugar. Let the sugar cool completely before moving to the next step.⠀ ⠀ Grind the Szechuan peppers in a mortar and pestle until they are crushed and the smell is starting to release.⠀ ⠀ Add the crushed pepper to a spice grinder along with 1 tablespoon of the roasted sugar. Pulse until the Szechuan peppers are even smaller in size and equally distributed throughout the sugar.⠀ ⠀ Pour into a food processor with the rest of the sugar and orange zest. Pulse until equally distributed and lay the sugar out on a baking sheet to dry.⠀ ⠀ Recipe Notes⠀ You can use regular sugar if you want. Roasted sugar can be used like regular sugar and it tastes less sweet and has a more caramelized flavor profile.⠀ ⠀ #diymocktailbar #thefeedfeed #meganwellsphotography #megiswell #saveur #foodwinewomen #imsomartha #cntravelereats #foodblogeats #sunsetmagazine #ediblemagazine #sonomacounty #sonomamagazine #bareaders #mywilliamssonoma #saveurmag #bakeandshare #bakersgonnabake #bakefromscratch #thebakefeed #thefeedfeedbaking #sweetcuisines #thesugarfiles #marthabakes #foodblogfeed #eattheworld #bakeit #rslove #bhgfood
  • First up in the series of infused sugar and shrub recipes I'm using in the #diyginbar is this Vanilla Bean Sugar. ⠀ ⠀ Once you open whatever container you end up storing it in, the vanilla aroma hits you and life is great 😌⠀ ⠀ You can find the link to the recipe in my profile @megiswell or you can hit save to come back to it later. ⠀ ⠀ Ingredients⠀ 2 cups raw sugar or regular sugar⠀ 1 teaspoon vanilla extract⠀ 1 vanilla bean halved and beans scraped out⠀ ⠀ Instructions⠀ Combine the sugar, vanilla extract, and vanilla beans in a food processor and pulse until combined. Lay out on a baking sheet and let dry. Store in an airtight container.⠀ ⠀ Raw sugar can be very hard to dissolve in liquid, even when it’s hot. If you are going to be using the sugar in drinks primarily, I would suggest using regular sugar. I grind mine in a mortar and pestle to make it easier to dissolve if I’ll be using it in drinks. You can also put it in a high-speed blender and pulse until the grains are finer.⠀ ⠀ I used this sugar in a Blackberry Shrub along with some Earl Grey tea 👌and you can muddle it along with fruit and herbs in your cocktail shaker for some extra flavor 🙌⠀ ⠀ #diymocktailbar #thefeedfeed #meganwellsphotography #megiswell #saveur #foodwinewomen #imsomartha #cntravelereats #foodblogeats #sunsetmagazine #ediblemagazine #sonomacounty #sonomamagazine #bareaders #mywilliamssonoma #saveurmag #bakeandshare #bakersgonnabake #bakefromscratch #thebakefeed #thefeedfeedbaking #sweetcuisines #thesugarfiles #marthabakes #foodblogfeed #eattheworld #bakeit #rslove #bhgfood

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