Position a rack in the center of the oven and preheat to 300 degrees F (150 degrees C). Spray a 12-cup fluted tube pan (such as Bundt®) with baking spray; set aside.
Beat softened butter in a stand mixer fitted with the paddle attachment on medium speed until creamy and light yellow in color, 4 to 6 minutes. Gradually add sugar, beating on medium speed until light and fluffy, about 3 minutes, scraping down the sides of the bowl as needed. Add eggs one at a time, beating just until combined.
Alternately add flour and milk, beginning and ending with flour, beating on low speed after each addition until batter is just blended. Add vanilla extract and peppermint extract; blend just until incorporated.
Transfer 1 cup of the batter into a small mixing bowl; stir in red food coloring.
Pour 1/3 of the uncolored batter into the prepared pan. Dollop with 1/3 of the red batter. Top with remaining uncolored batter and dollop with remaining red batter. Tap the filled pan gently on the counter to release any air pockets. Use a long skewer or off-set spatula to swirl the batter slightly.
Bake in the preheated oven until a long wooden pick inserted into the center comes out clean, 1 hour 45 to 55 minutes. Cool in the pan on a wire rack for 15 minutes, then invert onto the rack to cool completely, about 1 hour.
While the cake cools, beat softened cream cheese and butter in a stand mixer fitted with the whisk attachment on medium speed until light and fluffy. Slowly add powdered sugar, a little at a time, mixing on low speed, until all the sugar is incorporated. Add milk and vanilla extract; beat until smooth and creamy.
Drizzle frosting over the cooled cake. Sprinkle candies and peppermint bark over the frosting while it’s slightly wet. Let stand for 20 to 30 minutes before slicing.
Grease the baking pan like you mean it!
Soft buttermint “meltaway” candies and chocolate peppermint bark are sold during the holiday season, and can always be found at Cracker Barrel’s candy section in their stores. Amazon is another source.
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