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Combine the butter, brown sugar, and granulated sugar in a large bowl and beat with a mixer on medium speed until lightened in color and creamy, 1 to 2 minutes. Add the eggs one at a time, beating at low speed, until each is fully combined. Scrape the sides and bottom of the bowl, as needed. Add the vanilla and mix at low speed to combine.
Whisk together the flour, salt, baking soda, cinnamon, and oats in a medium bowl. Slowly add the dry ingredients to the butter mixture while mixing on low speed, scraping the sides and bottom of the bowl as needed.
Fold in the dried cherries, puffed rice, pepitas, and chocolate chips with a rubber spatula.
To bake immediately: Preheat the oven to 350°. Scoop the dough into 2 tablespoon-sized balls and place them on a parchment lined sheet tray, about 2 inches apart. Grease the bottom of a glass and press the cookies ½-inch thickness. Bake for 12 to 14 minutes, or until the edges are lightly golden.
To make ahead: Preheat the oven to 350°. Place the frozen cookie dough on the counter to thaw while the oven is preheating, about 20 minutes. Place the cookies 1 ½ inches apart. Grease the bottom of a glass and press each cookie to be ½-inch thick. Bake for about 15 minutes or until the edges of the cookie are lightly golden.