Rustic Pear Upside-Down Cake

I’m new to the world of upside-down cakes (umh, this is literally my first) but I’m awfully smitten. Not sure why it has taken me so long to jump on the bandwagon, but I’m grateful to my gig – contributing a recipe each month to Millerton NY’s Main Street Magazine – for getting me started on an upside-down cake roll. Often an idea for a recipe just comes to me – like last night when I couldn’t sleep and decided I needed to develop a recipe for coffee stracciatella ice cream (stracciatella is essentially what chocolate chip gelato is referred to in Italian – but the chocolate bits are not chunks or chips, but irregularly shaped shards that you make by dripping melted chocolate into your ice cream machine during the last minutes of churning – sounds amazing, right?). But I digress: sometimes an idea comes to me not due to insomnia, but due to a work deadline, like in this instance.Rustic Pear Upside-Down Cake | Jessie Sheehan BakesAs the deadline loomed, I knew my dessert would be pear-based, as I wanted to avoid the more obvious apple-forward sweets category, But am honestly, not sure why it inspired me to flip said pear dessert on its head, as it were. But I am so pleased it did (and hope you will be, too). This pear upside-down cake is oil-based, and so extremely moist, as well as easy to put-together. The fruit turns almost jam-like as it cooks, with lots of caramelized bits throughout, adding texture and just plain old-deliciousness, as only melted butter and sugar can do. 

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Rustic Pear Upside-Down Cake

Recipe Author Jessie Sheehan
Course Cake, Dessert, Desserts
Cuisine Cake
Servings 8 slices


For the caramel:

  • 4 tbsps unsalted butter
  • 2/3 cup light brown sugar
  • 1/4 tsp table salt
  • 1 tsp pure vanilla extract
  • 1/2 tsp freshly ground cinnamon
  • 2 tbsps granulated sugar
  • 2-3 ripe, but firm, pears Anjou or Bosc

For the cake:

  • 1 1/2 cups all-purpose flour
  • 1 1/2 tsp baking powder
  • 3/4 tsp table salt
  • 2/3 cup vegetable oil
  • 1 1/4 cup granulated sugar
  • 2 tsps pure vanilla extract
  • 1 egg
  • 1 egg yolk
  • 2/3 cup buttermilk


  • Preheat the oven to 350°F. Melt the butter in a 10-inch cast iron skillet over medium heat. Add the brown sugar and salt and cook until melted, stirring occasionally. Off the heat, add the vanilla and set aside.
  • Combine the cinnamon and sugar in a medium-sized bowl. Core and cut the pears into 1/4-inch slices (peeling is optional), place in the bowl with the cinnamon/sugar mixture, and toss to coat. Decoratively press the pears into the caramel, overlapping them slightly, until all of the caramel is topped with fruit. Set aside.
  • Whisk the flour, baking powder, and salt in a medium-sized bowl, and set aside.
  • Place the oil, sugar, and vanilla in a large bowl. Whisk to combine. Add the egg and yolk, and continue whisking until smooth. Add the buttermilk and whisk again. Add the dry ingredients to the wet, and using a rubber spatula, gently fold to combine. Do not over mix. Scrape the batter over the pears and gently smooth the top.
  • Bake for 38 – 43 minutes, rotating at the halfway point, until a cake tester comes out with a moist crumb or two. Immediately run a paring knife around the edge of the pan. Let sit for 5 minutes and then carefully invert the cake onto a serving platter. If bits of caramel or fruit stick to the bottom of the pan, scrape them off and place them back onto the cake.
  • Let cool until the caramel sets a bit, about 20 minutes, or cool to room temperature. Serve with vanilla ice cream or whipped cream. The cake will keep wrapped in plastic wrap on the counter for up to three days, but because it is excellent for breakfast, it likely won’t last that long.

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