Begin by getting the oven ready for baking: move oven racks around so that you have one rack in the center of the oven. Then preheat oven to 325F.
Stir 1/2 cup sugar and 1/4 cup of water in a small saucepan on the stove, over medium heat until the sugar dissolves.
Boil the sugar mixture until it turns golden in color, brushing any crystals that form on the sides of the pan with a wet brush. This should take about 7 minutes.
Immediately divide this mixture among 6 souffle cups or ramekins (use 1/2 cup or 4 fl oz size). Let cool.
Whisk pumpkin, eggs, remaining sugar, vanilla, cinnamon, allspice in a large bowl together.
Gradually whisk in the milk. Divide this mixture evenly among the 6 souffle cups.
Place souffle cups in a large glass baking dish such as a 9" x 12" Pyrex dish. Add enough water to baking dish to come halfway up the sides of the souffle cups.
Bake until the flan is set (about 55 minutes). Cool, then refrigerate at least 8 hours before serving.
Serve in souffle cups or remove and serve on plates. Enjoy!
Tip: You can reduce the sugar in Step 5 for a less sweet dessert.