Place the cream cheese and butter in a medium bowl. Mix with a hand mixer on medium speed until light and fluffy.
Add the flour and mix on medium speed to create a dough. Refrigerate the dough for 1 hour.
While the dough is chilling, place ½ cup water and ½ cup granulated sugar in a small saucepan. Bring to a simmer over medium heat.
Remove from the heat and add the cranberries. Let the cranberries steep for 10 minutes.
Drain the cranberries and place them on a sheet of wax paper to dry for 30 minutes.
Place ¼ cup sugar in a medium bowl and toss the cranberries gently to coat. Set aside.
Preheat the oven to 375 F.
Roll the chilled dough into 24 one-inch balls. Place one ball in each cup of a miniature muffin tin.
Press the dough evenly against the bottom and the sides of each muffin cup.
Place the pumpkin puree, evaporated milk, ¼ cup sugar, eggs, pumpkin pie spice, and salt in a large bowl. Mix with a hand mixer until smooth.
Divide the pumpkin mixture among each muffin cup.
Bake for 20–25 minutes, or until a toothpick inserted into the center comes out clean. Let cool completely.
When the bites are cool, place the heavy cream and remaining 1 tablespoon sugar in a mixing bowl. Mix on medium speed with a hand mixer until soft peaks form.
Place a dollop of whipped cream on top of each pumpkin pie bite and top with a sugared cranberry (or two). Serve.