Preheat oven to 350°F. Beat butter and brown sugar together until smooth. Add eggs one at a time, mixing after each addition. Add vanilla.
In a separate bowl, whisk together flour, baking soda, cinnamon, and salt. Gradually add to the butter mixture just until combined. Do not overmix. Stir in oats, cherries, and chocolate.
Roll into balls (about 1 inch in diameter). Bake for 16 to 18 minutes, or until bottom edges are lightly browned. Cool on pans for a few minutes, then remove to wire racks to cool completely.