Few foods symbolize a season like the winter squash. As soon as bright orange pumpkins and deep green acorn squashes dot the markets, our wardrobes are suddenly given permission to take on the same fall colors despite the thermometer reading. Granted, here in Texas the summer squash hangs on well into fall, but no matter. Just seeing the hard, fat little orbs of dense squashiness has me thinking of all the ways to welcome autumn to my palate.
The irony of the name ‘winter squash’ has not escaped me. I am assuming the fall-harvested squashes received their name from their blessed ability to keep over the winter. I can only imagine how extremely valuable they were in winters past, before electricity and cold-storage came along. In fact, the name “keeper” is added to some varieties, touting their ability to hold for long times in storage.

The two face off.
I bought a variety new to me from Stacey, called a “Taiwanese Keeper.” Stacey usually only plants heirlooms, so I wanted to compare this squash, which looked very pumpkin-like in shape, although not in color, to a store-bought “Pie Pumpkin.” These are the smaller pumpkin variety usually sold in the store as a cooking pumpkin, as opposed to the bin-sold jack-o-lantern types. I was going to use just two methods…oven roasting and grilling. I think steaming and boiling dilute the squash flavor, not to mention bypass the opportunity to carmelize the naturally present sugars.

Sliced for the grill, awaiting olive oil and salt.
The Grill: My hunch was that the keeper was going to be best on the grill and the pie pumpkin in the oven. So I reserved the top third of the keeper for the oven, and used just about a quarter of the smaller pumpkin for the grill. I began by slicing the squash into inch slices, or nearly so. I learned a few things:
a) Use a sharp knife. Ugh. I had to use too much force (my fingers are still here – yea!) and my slices were horribly uneven. There is more than aesthetics at stake here. It means that the slices are going to cook unevenly on the grill. So if you decide to grill your winter squash, using a sharp knife might keep you from a trip to the E.R.
b) don’t start a project like this when you promise your kindergartener that you are going to meet her for lunch. My squash was not ready when I noticed I was already late, so I had to make the unproven decision to move the squash away from the fire and hope that the indirect heat for 30 minutes was not going to ruin it.
c) if using a traditional grill, be sure and build your fire broadly. I am sure there is a better way to say that, but what I mean is think about the space required to spread out the squash. I made my fire with the image of the intact squash in my mind, forgetting how much space rings of squash would need once spread out. This forced me to overlap some…not desirable.
With these lessons learned, here is the method: Prepare your grill for medium-high heat, using the 3 second test. (The heat is about right when you can hold your hand above (not on!) the grate for about 3 seconds comfortably.) Slice your squash into 1 inch slices, brush with olive oil and sprinkle with salt. Oil the grill and lay slices directly above the heat. Flip after 5-10 minutes. (Note: I could not find a consensus on time…I read everything from 5 minutes per side up to 30! I think the reason for this is that each squash is different. My pie pumpkin slices were ready much sooner than the keeper.) Continue to grill until tender and nicely carmelized.

Like a steak!
Results: America’s Test Kitchen I am not, so my methods weren’t perfect, but I was really happy with the way the keeper turned out. I’m not sure exactly what the results would have been if I did not have to move it off of direct heat during my 30 minute kindergarten lunch, but what did turn out was perfect for cubing. It made about 5 cups of cubed squash. Lightly smoky, not overwhelmingly so. Gently carmelized on the outside. Firm, yet tender. The pie pumpkin did not, as expected, stand out with this method.
The Oven: I’ve seen people roast whole, sliced and halved squash for the oven. I think your method will depend on how you want to serve it. I had puree in mind, so I just halved the pumpkin, minus a slice or two from the middle, scooped out the membranes and seeds, and put the cut halves face down on an oiled cookie sheet.
Had I wanted oven roasted squash for a side dish, I would have sliced, oiled, and salted the squash. I can’t think of a single reason I would want to roast one whole. Besides, you can’t roast the seeds that way!
Preheat your oven to 400 F. Roast the halves face down for 45 minutes up to an hour or more. You want to see a nice, brown, carmelized bottom when finished, and the tops will look collapsed. Scoop out the cooked flesh when cool enough to handle.
Results: The pie pumpkin didn’t need pureeing at all. Very smooth and sweet. The keeper had a stringier, dryer texture, similar to a spaghetti squash, but when pureed in a food processor, it became silky smooth; not as sweet as the pumpkin but very mild and slightly butter-y. The pie pumpkin lived up to its name…perfect for a smooth pie. The keeper would be best as a pureed side dish or in a bread. I was amazed at the yield of the keeper, too. The top third made 2.5 cups of puree. The pie pumpkin only yielded 2 cups.

Conclusion: The method you choose should have the end result in mind. If you plan to use the squash as an eye-appealing side or in a savory dish which requires a second cooking, such as a white sauce lasagna, the grilling method will suit your purposes splendidly. The squash will be tender yet still retain its shape. I would also choose this method for a cold salad or quesadilla. For desserts and purees, the oven method will work best. The squash breaks down into a creamier texture and the deeply carmelized flavors will add a sweeter touch.