Place the cherries in a bowl and cover them with the bourbon. Microwave for 1 minute then let them sit and soak for at least 10 minutes – or even longer.
Preheat the oven to 325 degrees F. Line a baking sheet with parchment paper.
In a bowl, stir together the flour, cinnamon, baking soda and salt. Add the coconut and stir it into the flour.
In the bowl of your electric mixer fitted with a paddle attachment, beat the butter and sugar until fluffy, about 5 minutes. Add the maple syrup and molasses and mix to combine. Add the egg and vanilla and beat until well combined, scraping down sides of bowl as needed. With the mixer on low speed, add the flour mixture in two batches; mix until just combined. Add oats and cherries and remaining bourbon if you’d like, and mix until combined. Stir in the chocolate chips.
Using a 2-inch ice cream scoop or scoop 3 tablespoons, drop the dough 2 inches apart onto a baking sheet. Bake until edges begin to turn golden brown, 15 to 17 minutes. Do not overbake even if the center looks a bit soft, they will set while cooling. Let cookies cool on the baking sheet until firm enough to remove to wire racks, about 2 minutes.
Cookies can be kept in an airtight container for about 2 weeks. They also freeze well in a airtight bag for up to 3 months.