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Beat heavy cream using an electric mixer until stiff peaks form, about 3 minutes. Stir in sweetened condensed milk and vanilla until thoroughly combined. Mix in candy cane pieces, mixing just enough so they start to leave pink streaks in the ice cream. Fold in peppermint bark and chocolate chips, setting aside a few to sprinkle on top of the ice cream. Pour the ice cream batter into a loaf pan, add remaining chips and bark, and place in the freezer until firm, about 6 hours.