Save the cinnamon-sugar and marshmallows for holiday cookies.
I grew up assuming that I loathed squash. It wasn't a vegetable I recall being in our dinner repertoire (maybe I've blocked it out), but when I'd encounter it in the wild at a friend's house or a holiday gathering, it was inevitably served one way: sweet. Perhaps there was a mandate that went out over channels I was not privy to because my street didn't get cable until kind of late in the game, but if squash appeared on the table or buffet, it was marooned in a bay of butter, lashed with brown sugar and cinnamon, and worst case scenario, completely asphyxiated under a goopy layer of marshmallows. Whatcha trying to hide, squash?
Squash was not the culpable party here. Squash—and we're talking winter squash here—is just hanging out, living the cucurbit life, being all nutrient-dense and underestimated. It doesn't need to be sugar-smacked or cream-blitzed to be delicious. All it needs is a little heat, patience (not that much), and seasoning to become your favorite savory side.
Pick your squash, any winter squash, and decide how much effort you'd like to put into it. You'll almost definitely want to peel a butternut or hubbard squash, but delicata squash skin softens nicely and can add a lovely textural element. You decide. Either way, preheat the oven to 375°F, slice the squash open and scrape out the seeds. Wash and roast them or compost them, but don't waste them.
Cut the halves into manageable slices and then—this is key—resist the urge to make neat cubes. Cut those slices at weird, multiple angles like you're trying to make Dungeons and Dragons dice, because the more edges and surfaces there are, the more opportunities there are for crispness. Toss these pieces in the oil of your choice (I like the nuttiness that a good dark sesame oil can bring, but only you can determine your squash destiny.) and place them in a single layer on a baking sheet, ideally not touching.
Here's where things get wacky. Think of roasted squash chunks as the blue jeans of sides—they're a great foundation, and you get to dress them up however you'd like. You'll definitely need salt, so hit 'em with a good sprinkle of that, and then choose the direction you'd care to go. Lately for me it's been either a solid dusting of Aleppo pepper and sumac, or a three-pronged punch of cumin, turmeric, and a mild curry blend. I went through a vadouvan phase that only halted because I ran out. If I'm feeling all Thankgiving-y, I deploy Bell's poultry seasoning, which is a proprietary mix of rosemary, oregano, sage, ginger, marjoram, thyme, and pepper. If the evening is just going that way, I bust out the Paleo faux-Doritos spice, go nuts with the furikake, or splash on some fish sauce, vinegar, or both. I have deployed bottarga on occasion and regret nothing. A multi-herb pesto would be great, but I rarely have the energy. It's your spice journey and I cannot take it for you.
Set a timer for 15 minutes because you will forget the squash in the oven and all the chopping will be for naught. Flip the squash chunks around on the tray so different parts have a chance to crisp, and set the timer for 10-minute intervals, flipping each time and adding oil as needed, until the squash is crisp and brown on the outside and tender on the inside. Enjoy it then and if—miraculously—there are leftovers the next day, heat them in a skillet with a little oil, scoop them into a bowl, and fry an egg or two in that same pan. Breakfast is so very served.