In a medium bowl, whisk flour, cinnamon, sugar and salt together. Put in a food processor and add the cubed cold butter. Pulse until it resembles small peas.
In a separate small bowl, beat the egg with the milk. Add the egg mixture to the food processor with the dough. Pulse until just mixed. Spread some flour on a surface and knead the dough until it comes together well. Divide into two balls, wrap in plastic, and place in refrigerator for about 30 minutes.
While dough is chilling, line 2 - 9x13 baking pans with parchment paper and preheat oven to 350 degrees F.
In medium bowl mix pumpkin, cream cheese, brown sugar, egg, pumpkin pie spice and cinnamon together. Place in refrigerator.
Get out your dough and on a well floured surface, roll out to about 1/8 thickness. Trim dough with a pastry cutter, or a pizza cutter will work. You can cut your dough in 3x5 inch rectangles. You should be able to roll out about 9 rectangles. Then place on parchment paper.
Next you can roll out the second piece of dough and cut the same way. Brush one side of 9 rectangles with either melted butter or beaten egg- this will help hold together the top layer of dough. Take out your pumpkin-cream cheese mix from the refrigerator and place 1 tablespoon of mix onto each brushed dough rectangle. Top with another piece of dough and use a fork to seal the edges and poke three holes on top to vent. Brush with melted butter.
Bake for about 20 – 25 minutes or until the top is golden brown. Cool on wire rack.
Once pop tarts are fairly cool, mix together cream cheese, maple syrup and cinnamon in a small microwavable bowl. Microwave on high for 20 seconds. Stir until creamy and drizzle on top of pop tarts.
Serve immediately while glaze and pop tarts are still warm.