Preheat oven to 350 degrees. Lightly spray a 9″ round baking pan (a 9×12 pan works, too) with cooking spray. Line the bottom with parchment paper.
Melt 1/4 cup butter; stir in 1/4 cup brown sugar. Spread evenly over parchment paper.
In a pan of boiling water, boil 1 cup of cranberries for 3-5 minutes until they begin to pop. Drain and set aside.
Peel and slice the pears, arranging the slices on top of the brown sugar mixture. Sprinkle the top with the drained cranberries.
Whisk together the flour, cornmeal, baking powder, baking soda, salt, and sugar in a large bowl. Whisk together the buttermilk, eggs, almond extract, and melted butter in a medium bowl. Add the wet ingredients to the dry ingredients and whisk to combine.
Transfer the batter to the prepared pan, spreading on top of the pears and cranberries. Bake for 35-40 minutes until done. Remove from the oven; transfer to a wire rack. Cool for 10 minutes.
Meanwhile, whip 1 cup of heavy whipping cream until creamy and thick, adding in the brown sugar and vanilla. Set aside.
Run a knife blade around the edge of the cake to loosen it from the pan. Invert the cake onto a serving plate. Lightly tap the bottom of the pan to loosen the cake, then lift the pan.
Peel off the parchment paper. Serve the cake warm or at room temperature.
Top with whipped cream right before serving (optional).