There are several different kinds of winter squash and many of them have a very unique taste. Butternut squash is probably the most popular squash and easiest to find. Acorn and spaghetti squash are also found in most food stores. Kabocha squash is delicious as well, but harder to find.
Squash should be big, usually the bigger the better. It should be very dry, hard, difficult to cut and heavy for its size. The darker it is on the inside, the better. If the skin of the squash is dark (spaghetti & butternut) it usually means it’s darker and riper on the inside.
Cut squash in half (lengthwise), scoop out the seeds (like a pumpkin) and place the open side down on a baking pan or for faster roasting- cut into 1” cubes. Do not add any water to the pan, that’ll steam the squash instead of baking it. Some squash like spaghetti squash can be very difficult to cut. I usually stick the knife straight into the middle so that it’s sticking up, like planting a flag. Then I pull the knife down, towards me, while twisting it left and right. You can also use a small handsaw (no joke).
Bake it in your oven @ 400F for at least an hour for whole squash and about 30 minutes for 1” cubes. You want it to actually “bleed” and that only happens when you cook it for a while. The label and most recipes will say to cook it for a half an hour or so or even to microwave it. Trust me, you do not want to do this. You want to dry the squash out as much as possible, the less water it has the sweeter it is. Basically you want to take the squash out right before the bottom starts to burn. You want the squash to caramelize. The squash will be much more satisfying as well when it’s not all watery, particularly when eaten cold.
I prefer squash cold, so I cook it the night before I eat it and let it cool then refrigerate it. A lot of people season squash with cinnamon, I also like to add savory spices and other vegetables along with the cinnamon, like fresh thyme and onion. Use your imagination, as I’ve said before, experiment, you’ll be amazed at what you can create!
~ Chef Jack






December 24th, 2009 at 11:29 am
Chef Jack,
Do you spray the pan with PAM or anything before you place the squash on it to bake?
January 5th, 2010 at 6:52 pm
Hi Erin,
Yes, you can spray the pan with PAM first — I usually do. I’ll add that to the article. Thanks for the question!
Yours in Good Health,
Chef Jack
February 7th, 2011 at 9:41 am
[...] Tips for Roasting Winter Squash ~ Chef Jack gives you some excellent tips for roasting various winter squash, like butternut, acorn and spaghetti squash. [...]