Add dried cherries and amaretto to a small bowl. Microwave for 30 seconds to warm amaretto and set aside to allow cherries to absorb some of the amaretto and plump.
Meanwhile, add 1/4 cup brown sugar, flour, cinnamon, and salt to a small bowl Toss to combine. Cut 1/4 cup butter into the flour mixture using a pastry cutter until it resembles coarse meal. Add oatmeal and almonds and toss to combine. Set aside.
Melt remaining tablespoon of butter in a small cast iron skillet over medium heat. Scoop the macerated dried cherries out of the Amaretto and add it to the pan along with the sliced peaches, cherries and remaining 2 tablespoons of brown sugar. Stir for 2-3 minutes until the brown sugar dissolves.
Add the cornstarch to the reserved Amaretto and stir to combine.
Add the Amaretto slurry to the peach mixture and heat until the liquid is bubbly and thickened slightly. Remove pan from heat and sprinkle crisp mixture over the fruit.
Bake for 20-25 minutes, until crisp is golden brown.
Remove from oven and cool for 5-10 minutes before serving.
Serve with a scoop of your favorite ice cream while warm.