Chocolate Cherry Amish Sugar Cookies are soft, puffy, buttery, melt-in-your-mouth sugar cookies, crammed with melty chocolate chips and sweet maraschino cherries, and then generously iced with cherry frosting! Made with common pantry ingredients, these Chocolate Cherry Amish Sugar Cookies are super, super simple to whip up, and feed a crowd!
As noted above, drain the maraschino cherries, reserving the juice (!), finely mince the cherries, and then pat/squeeze VERY dry. Set aside.
In a large mixing bowl, beat the butter, oil, and sugars until combined.
Beat in eggs, vanilla extract, and cherry extract.
In a large bowl, whisk together flour, baking soda, and cream of tartar.
Add flour mixture to the butter mixture in 2 or 3 additions, beating until just combined after each addition. Do not overmix or dough will be tough.
Beat in cherries until just distributed. Again, do not overmix.
Using a spatula, fold in chocolate chips.
Line baking sheets with parchment paper or silicone baking mats.
Drop dough by teaspoonfuls onto baking sheets.
Bake at 375 for 8-11 minutes, or until edges and bottoms are lightly browned.
Remove to wire racks to cool.
Whisk together butter, 1/3 cup maraschino cherry juice, vanilla extract, and cherry extract.
Stir in 4 cups powdered sugar, mixing until smooth.
Add additional maraschino cherry juice or powdered sugar, as needed, to achieve a thick, but spreadable consistency. It should be thicker than a glaze, and it shouldn't run off the cookie, but should be easily spreadable.
Because this icing contains melted butter, it "sets". If you find that it's starting to get too thick while you're icing the cookies, you can pop it in the microwave for 5-6 seconds. That's it -- only a few seconds will thin it back out.
Ice the cookies, decorate with sprinkles or chocolate jimmies, if desired, and allow to set.
Store cookies in airtight containers in a cool, dry place. Stack cookies with parchment paper or foil in-between layers. Cookies will keep for about a week.
These are good for at least a week, but best within the first 3 days. After 3 days, they get crumbly and a bit on the drier side - still a delicious cookie though.
These freeze really well! Iced or plain, they freeze beautifully.
I've made these Amish Sugar Cookies into Pistachio Coconut Amish Sugar Cookies, Pecan Praline Amish Sugar Cookies, Iced Maple Amish Sugar Cookies, Pumpkin Spice Latte Amish Sugar Cookies, Iced Chai-Spiced Amish Sugar Cookies, Iced Almond Cookies, Iced Lemon Amish Sugar Cookies, Iced Orange Amish Sugar Cookies, Toasted Coconut Amish Sugar Cookies, Coconut Oil Amish Sugar Cookies, Thin Crispy Amish Sugar Cookies, Chocolate Chip Amish Sugar Cookies, Butter Pecan Amish Sugar Cookies, Cranberry Orange Amish Sugar Cookies, Eggnog Amish Sugar Cookies, and Peppermint Amish Sugar Cookies..... the list goes on!