You can bake this in a 9-inch pan, which yields nine perfectly square pieces. Or, use a 9- or 9½-inch cast iron skillet, which results in a crunchier glaze. Either way, this is fun to assemble and even more enjoyable to eat!
Find this recipe and many more delicious treats in The Old Farmer’s Almanac Everyday Baking cookbook.
For topping: Line a dinner plate with paper towels. Lay the pineapple slices on the plate and blot them dry on both sides. Set aside. Lightly butter a 9-inch square (preferably nonstick) baking pan (see note below). Combine the butter and maple syrup in a small saucepan over medium heat. When the butter melts, stir in the brown sugar. Bring to a low boil and cook for 30 seconds, stirring. Pour the mixture into the buttered baking pan. Tilt the pan to spread the mixture. Lay the pineapple slices in three rows and put a cherry into the middle of each slice. Press one pecan half, if using, in each gap between the pineapple slices. Set aside.
Note: If you’re using a round skillet, heat the butter–maple syrup–brown sugar mixture right in the pan. Make a ring of pineapple slices, just touching, with one in the center, and proceed as directed with the cherries and pecans.
For cake: Preheat the oven to 350°F. Using an electric mixer on medium-high, cream the butter, gradually adding the sugar. Add the eggs, one at a time, beating well after each addition. Beat in 1⁄3 cup of buttermilk, the molasses, and the vanilla. Sift the flour, baking powder, baking soda, salt, and cinnamon into a bowl. Add half of the dry ingredients to the creamed mixture and beat until smooth. Add the remaining buttermilk, beat to blend, then add the remaining dry ingredients and beat to combine. Scrape the batter over the pineapples and smooth with a spoon. Bake on the center oven rack for 35 to 40 minutes, until the center of the cake springs back when touched.
Put a platter or baking sheet over the top of the pan. Carefully invert the cake onto the platter and remove the pan. Replace any pieces of pineapple that may have stuck. (Caution: When turning the cake out of the pan, wear long sleeves and oven mitts in case some of the hot glaze leaks out.) Cool for at least 10 minutes before serving.