These cookies are oddly addictive. Well – chocolate and cinnamon – I guess it’s not that odd. But it’s more than that, I tell you! There’s something about the subtly sweet pumpkin cookie part, which shines through the more assertive flavors of cinnamon and chocolate, that makes you want more. That, and, they’re spirals! With gooey cinnamon-y chocolate-y bits that you get to when you peel them apart. What could be more fun to eat than that? I should say, in the interest of full disclosure, I accidentally added too much pumpkin purée, which meant that I had to compensate by adding too much flour, which ultimately produced a very dense cookie. This recipe is adjusted to make a slightly lighter cookie, but it will still have that pumpkin pie-tenderness.
Here’s The Great Pumpkin Waltz performed by the Vince Guaraldi trio.

2 cups flour
1 stick (1/2 cup) unsalted butter, cut into small cubes
1/2 t. salt
1 t. baking powder
1/4 t. ginger
1/4 t. nutmeg
1/4 t. allspice
2/3 cup brown sugar
1 t. vanilla
1 egg
1/2 cup pumpkin purée (+/-)

For the filling…

3 T soft butter
1/2 cup brown sugar
1 1/2 t. cinnamon
1 cup dark chocolate chips.

Make the dough…

Combine the flour, sugar, salt, spices, baking powder in a big bowl. Add the butter and work with your fingers till it resembles coarse crumbs. Stir in the egg, vanilla and pumpkin. You should have a stiff but workable dough. If it’s too dry, you can add a little more pumpkin.

Knead for a few minutes so that everything is well incorporated and mixed, and then wrap the dough in foil or plastic and put it in the fridge for an hour or so.

Combine the softened butter, the sugar and the cinnamon.

Roll the dough to be about a foot wide, and however long it needs to be to make the dough about 1/4 inch thick – should be close to 2 feet. Sprinkle the dough with the cinnamon/sugar/butter mixture, trying to spread it as evenly as possible. Then sprinkle with the chocolate chips. Roll the dough up starting at the long end until you have a log about 1 1/2 inches across.

Cut this into 1 inch slices, and put these onto a baking sheet, spiral side down, leaving an inch or so between them.

Bake at 375 for about half an hour, till they’re slightly puffed and start to brown. You can turn them over about 10 minutes before they’re done to make sure both sides get browned and nicely caramelized. (The bottom side is the one that gets more brown).