Robert Wemischner

Yield: Serves 4 to 6, depending on the size of baking containers used, with enough extra Cranberry Shortbread Cookies to last a few days

Here is a satisfying seasonal dessert which takes time (roasting of the squash) and patience (oven time and chilling time for the pudding, if you are not serving it warm) but is far from difficult. Depending on the size of the squash you are using, baking time will vary. Be sure to allow enough time so that it is well cooked and tender. And then, once you have mixed all of the ingredients together and made the caramel, all that’s left to do is a relatively unsupervised baking of the pudding. The dough for the cookie accompaniment is simple to make and may be made a few days in advance and then chilled. In this case, remove the prepared dough from the refrigerator, cut and then bake on the day you wish to serve the dessert. (The dough, well wrapped, will keep in the freezer for up to a month).

For the pudding:

7 ounces cooked, peeled and seeded kabocha squash**
4 ounces eggs (approximately 3 large eggs)
2 ounces pure maple syrup (the darker Grade B has more flavor)
8 ounces whole milk
2 ounces heavy cream
1 t. pure vanilla extract
1/4 t. ground cloves
1/4 t. ground allspice
1/2 t. ground ginger
1/2 t. ground cinnamon
Pinch salt

Roast the squash on a cookie sheet in a preheated 375 degree F. oven until very tender. Test periodically by poking with a skewer or the point of a knife. (Roasting time will vary depending on the size of the squash; for the pudding, you will only use part of a kabocha squash; reserve the rest, roasted or uncooked for another use). Then cool briefly before removing and discarding the skin and seeds.

In a food processor, puree the cooked squash. Add the maple syrup, milk, cream and vanilla and process to blend. Then add the eggs and pulse to combine. Add the spices and salt and pulse again to blend. Avoid over mixing which will lead to undesirable aeration of the mixture. Set aside and make the caramel.

**Generally speaking, in the case of kabocha squash, you will yield an amount of usable squash slightly less than half of the original weight of the uncooked squash, as purchased. Therefore, to yield 7 ounces of cooked squash, start with a squash that weighs at least one pound. Most butternut squash have a somewhat higher ratio of usable flesh to seeds and skin so you would need to start with a less than a pound of it, as purchased, to yield the required 7 ounces called for in the recipe.

For the caramel:

4 ounces (1/3 cup) granulated sugar
2 ounces (1/4 cup) water

Place the sugar and water into a heavy small saucepan. Over medium heat, cook until the mixture turns golden brown. Using heat proof mitts or a potholder, grab the handle of the pot and swirl the caramel to be sure that it is coloring evenly. Then carefully pour a small amount of it into each mold, coating the bottom and sides of the molds as evenly as possible. Set the molds aside to cool briefly.

Now fill the caramel-lined molds with the pudding mixture. Place the puddings into a pan large enough to accommodate them. Pour hot water into the pan to come halfway up the sides of the molds and then bake in a preheated 350 degree F. oven for approximately 50 minutes. The puddings will be slightly puffy and feel almost firm to the touch. If you wish to serve them lukewarm, unmold them onto serving plates. You might need to run a small knife around the edges of the mold to release them but be careful not to mar the sides of the puddings. If you have made the cookies in advance, you could serve a Cranberry Shortbread cookie or three on the plate with the puddings.

If you wish to serve the puddings chilled, refrigerate for at least two hours (you may hold them for the next day, refrigerating them overnight). In this case, make the cookies while the puddings are chilling. Then, when you wish to serve the puddings, dip the molds into hot water briefly to warm the caramel slightly. If necessary, run a small knife around the edges of the molds being careful not to mar the sides of the puddings.

For the Cranberry Shortbread cookies:

Yield: approximately 32 cookies 1-1/2 inches round or square by 1/4 inch thick

6 ounces (1-1/3 cups) all-purpose flour
1 t. ground ginger
Generous pinch of salt
4 ounces (1 stick) unsalted butter, at room temperature
2 ounces (1/3 cup) granulated sugar
1 whole large egg
2 ounces (1/2 cup) dried cranberries, soaked briefly in hot water, drained and then tossed with 1 t. grated orange or tangerine zest

Sift the flour, ginger and salt together and set aside.

In the bowl of an electric mixer outfitted with a paddle attachment, cream the butter until light. Add the sugar and mix to blend. Then add the egg and mix until it is absorbed. With the mixer on low speed, add the dry ingredients and mix only until they disappear, scraping the bottom and sides of the bowl to be sure that all ingredients are well incorporated. Add the cranberries and then remove the dough from the bowl. Place it on a piece of parchment paper and using the paper to facilitate the process, form the dough into a rough log, measuring approximately 8 inches long by 1-1/2 inches in diameter. Place the dough into the freezer and chill until it is firm. After it has chilled sufficiently, you may flatten the cylinder into a four-sided shape if you wish the cookies to be shaped like tiles.

Preheat the oven to 350 degrees F.

With a heavy knife, cut the dough into approximately 32 cookies of even thickness. Place the cookies onto parchment-lined sheet pans spacing them about 3/4 inches apart. Bake for approximately 20 minutes, or until golden brown. Allow to cool and then store in a container with a tight fitting lid.