Begin by slicing the pear in half and removing any overly soft pulp, seeds, and the stem.

Roughly dice the pear and place it in a medium bowl.

Mash the pear thoroughly using a fork or a potato masher until it is well broken down.

Transfer the mashed pear into a fine mesh strainer set over a wide-mouthed measuring cup or another bowl. Press the pear pulp firmly against the strainer to extract as much juice and pulp as possible.

Once you have extracted the pear juice, add the bourbon, maple syrup, lemon juice, vanilla extract, and allspice to the juice.

Add ice to the mixture and stir vigorously until all ingredients are well combined and chilled.

Fill two glasses with ice and evenly divide the pear bourbon mixture between them.

Serve immediately and enjoy the warm, spiced flavors of this autumnal cocktail.