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30 minutes preparation time, plus an hour to bake the pumpkin and 30 minutes to chill the dough
approximately 40 minutes cooking time
For the dough:
1 1/3 cups all purpose flour
1/4 cup confectioners' sugar
1/2 teaspoon salt
1 stick (8 tablespoons) unsalted butter, frozen or chilled and cut into about 10 pieces*
1 egg
For the filling:
1 small sugar pumpkin
4 tablespoons unsalted butter
1/2 cup dark brown sugar
1/2 teaspoon sea salt
1 teaspoon vanilla
vanilla ice cream for serving (optional)
First, cook and prep the pumpkin: Preheat oven to 400 degrees. Cut off the top of the pumpkin with a serrated knife. Wrap the pumpkin in foil and bake until it begins to soften, about 40 minutes.
Remove the pumpkin from the oven and carefully unrap the foil. When the pumpkin is cool enough to handle, cut it in half from top to bottom and scoop out the seeds. Peel off the skin with a potato peeler. At first, this will seem nearly impossible because the skin is quite hard. Persevere. Once you get going, you will conquer that little pumpkin and the peel will be off in a couple of minutes. Slice the pumpkin into half inch sections from top to bottom. The flesh will be easy to cut but still quite firm.
While the pumpkin is cooking, make the dough: *You have two options here for making the dough. You can use the traditional food processor approach or a new technique that I just learned from Amanda Hesser at Food52. For Amanda's approach, whisk the flour, confectioners' sugar, and salt together in a medium-sized bowl. Using a stick of frozen butter, unwrap one end and grate it on the largest holes of a box grater. The butter will curl off into small shavings. Keep unwrapping the butter and grating until you have grated the entire stick. Add the butter to the flour mixture, crack the egg on top, and lightly scramble it. Mix everything together with your hands, breaking up any large pieces of butter. Push the dough into the shape of a ball and smash the ball onto the counter. All of the flour may not incorporate at this point, or the ball may crumble apart, but stick with it. Smear the ball across the counter to evenly incorporate the butter. As you do this, work in any flour that didn't incorporate initially. Just do this for as long as it takes to work in all the flour; don't overwork it.
To make the dough in a food processor, pulse the flour, confectioners' sugar, and salt together in a food processor. Add the butter and pulse until the butter ranges in size from that of a small pebble to that of cornmeal. Empty the flour mixture into a bowl, and crack the egg on top. Lightly scramble the egg and then, using your hands, work it into the dough until the dough starts to come together.
Roll the dough into a ball, and then flatten it into a disc. Wrap it in plastic wrap and refrigerate it for at least 30 minutes and up to a couple of days.
Assemble and cook the tart: When you are ready to cook the tart, turn the oven to 400 degrees.
Unwrap the dough and roll it out into a circle that is an inch or two larger than the diameter of your pan.
Heat the butter in an 8 or 9-inch oven-proof skillet over medium heat. When the butter has melted, stir the sugar and salt into the butter and spread them evenly across the pan.
Add the pumpkin slices one next to the other around the pan. Once you have finished the first layer, fit as many additional slices as you can in a second layer, filling in the gaps between the pumpkin pieces from the first layer. Squeeze in as many as you can because they will reduce slightly in size as they cook. Cut a few sections to fit into the middle of the tart.
Turn the heat up to medium-high and cook the pumpkin until the sugar turns a rich, dark brown and bubbles, about 5 minutes. Rotate the pan if needed to ensure that the sugar browns evenly. Sprinkle the vanilla over the top of the pumpkin and remove the pan from the heat.
Lift the dough with a spatula or a rolling pin and carefully drape it over the pan. Taking care not to burn your fingers, tuck the edge of the dough along the side of the pan. If you have measured accurately, the dough should just fit with a bit extra to slip down into the sides. If you do what I usually do and roll it a bit too big, just squeeze it into the pan. Don't worry if the dough is a bit lumpy because this will be the underside of the tart when you are done. Place the pan in the oven and let it cook until the crust is lightly browned, 25 to 30 minutes.
Remove the pan from the oven and let the tart cool for 15 minutes or more. Place a large serving plate over the top of the pan. With oven mitts or pot holders, pick up the pan with the plate on top and quickly flip the pan over so that the tart inverts onto the plate. I recommend that you do this over a surface that is easy to clean (or the sink) because more than once a bit of caramel has oozed out of the side as I flip the pan. Serve warm or at room temperature, ideally with vanilla ice cream.