Heat the oven to 375°F and line a large baking sheet with parchment paper. Assemble the pastry directly on the lined pan so the shaped candy cane does not need to be moved.

Unroll the crescent dough and arrange the pieces into a candy-cane shape, overlapping the seams and leaving a wide center area. If using a 16-ounce package of crescent dough sheets, cut 1-inch strips along both sides while leaving the middle intact.

Spoon the cherry pie filling down the center of the dough. Keep the layer narrow and avoid overfilling because extra filling may leak as the Danish bakes.

Fold the dough strips diagonally over the cherry filling, alternating from side to side to create a braided appearance. Curve one end of the dough to form the hook of the candy cane.

Bake for 22–28 minutes, rotating the pan halfway through if needed, until the pastry is puffed and deep golden brown. If the dough becomes soft while shaping, chill the assembled Danish for 10 minutes before baking.

Cool the Danish on the baking sheet for at least 10 minutes. Letting it cool until just warm helps the filling settle and allows the glaze to remain visible instead of melting away.

Whisk the powdered sugar with 1 1/2–2 tablespoons milk and the vanilla or almond extract until smooth. Drizzle the glaze over the cooled Danish, then slice and serve.