Using a food processor, add flour, brown sugar and salt; pulse until well combined.

Cut butter into small cubes and add to the food processor; pulse until a crumbly mixture forms.

Add vodka and 2 Tbsp of water; pulse until well combined. Continue adding water 1 Tbsp at a time (and pulsing) until dough comes together in a ball.

Shape dough into a disc and wrap with plastic wrap; refrigerate for at least 2 hours. (Note: Dough can be made the day before and refrigerated overnight.)

Preheat oven to 400°F.

Working on a well-floured surface, roll pie dough into a 12” circle.

Transfer pie dough into pan and gently press dough into pan; Leave ~1” of overhang on all sides

Fold excess dough under itself and use 2 fingers to crimp the edges. Refrigerate dough for at least 15 minutes.

Remove dough from refrigerator and use a fork to dock the dough every ~½”. Place foil on top of dough and fill with pie weights or coins.

Bake for 15 minutes.

Remove foil (and weights) and continue baking for 5 more minutes.

Place chocolate chips in a heat proof bowl; set aside.

Using a microwave, heat ¼ cup of cream until hot. Pour hot cream over chocolate chips and let stand for 1 minute.

Add peppermint extract and stir until smooth; set bowl aside to cool.

Using an electric mixer, whip remaining ¾ cup of cream and powdered sugar until stiff peaks form.

Using a spatula, fold the whipped cream and crushed candy cane into the chocolate mixture. Transfer filling into the baked pie shell.

Using a medium bowl, add whipping cream, powdered sugar and vanilla extract; whip until still peaks form.

Using a spatula, fold ½ of the crushed candy canes into the whipped cream.

Spread whipped cream evenly on top of the chocolate filling. Cover pie loosely with plastic wrap and refrigerate overnight.