Preheat oven to 325 degrees F. Line two baking sheets with parchment paper.
Beat butter and brown sugar in a large bowl for 1-2 minutes until creamy and light.
1/2 cup salted butter, 1/2 cup light brown sugar
Add eggs, milk, and vanilla. Beat again.
2 large eggs, 1/4 cup milk, 1 teaspoon vanilla extract
Add flour, baking soda, cinnamon, and salt. Mix just until combined, scraping the bottom and sides of the bowl. The mixture will be very soft.
1 1/2 cups all-purpose flour, 1/2 teaspoon baking soda, 1/2 teaspoon cinnamon, 1/4 teaspoon salt
Add chopped nuts, candied cherries, raisins, pineapple, and dates. Stir just until the fruit and nuts are evenly dispersed throughout the cookie dough.
2 cups chopped walnuts and/or pecans, 1 cup candied cherries, 1 cup raisins, 1/2 cup dried pineapple, 1/2 cup dates
Use a small cookie scoop to drop mounds of the dough onto the prepared baking sheets, spacing them a couple inches apart.
Bake for 12-15 minutes until golden brown and no longer glossy on top. Let cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
To glaze the cookies, whisk together powdered sugar and enough milk to create a thin glaze that drizzles off the whisk and melts in on itself immediately. Dip the top of each cookie in the glaze, then return them to the wire rack to dry for 2-3 hours so the glaze can set up.
3/4 cup powdered sugar, 2-4 Tablespoons milk