Make Nonnie's Kentucky Derby Pie tonight: a gooey maple, bourbon, pecan and chocolate pie to share.
Preheat the oven to 375°F and press your pie crust gently into an 8–9 inch fluted pie plate so the edges are even and the base sits snugly; set the plate on the painted pine surface while you assemble the filling. Keep small vessels ready for the liquids (maple syrup in a small glass jug, bourbon in a clear tasting glass) and a tiny ramekin for the kosher salt—this keeps everything tidy and within reach as you work.
In a large bowl, cream the room-temperature butter with the granulated sugar until pale and slightly aerated, then beat in the eggs one at a time until each is fully incorporated. Pour in the maple syrup, bourbon, vanilla, and salt and mix just until the mixture becomes a glossy, pourable custard—thick but with a slow ribbon when the spatula lifts. Fold in the semi-sweet chocolate chips and the raw pecans until they are evenly suspended in the batter, visible as dark chocolate flecks and warm brown nut pieces throughout the amber custard. This is the key visual milestone: a shiny, nut-studded, slightly viscous batter, thick enough to mound but fluid enough to settle when poured.

Press the prepared pie crust into the pie plate if you haven’t already, pour the studded batter into the crust so nuts and chips distribute evenly, and transfer to the oven to bake for 55–60 minutes—it's fine if the center stays a little jiggly when you remove it. Let the pie cool slightly on the painted pine surface so the filling sets just enough to slice; the top will become deep golden with a glossy, caramel-like sheen around whole pecans and chocolate pockets.
In a chilled mixing bowl, whip the heavy cream to stiff peaks, then gently fold in the tablespoon of bourbon and tablespoon of maple syrup until the cream is smooth, aromatic, and holds its shape. Serve a generous swirl of this bourbon cream atop the warm pie or alongside each slice—its soft ivory peaks and subtle boozy maple aroma contrast beautifully with the pie’s warm nutty tones and glossy filling.
