Forever Roasted Squash with Crispy Sage

8 ingredients•Prep: 15 mins•Cook: 3 hrs

Santa Anna

•

June 11, 2025

Squash is almost always my choice for “orange vegetable.” While it seems very unlike me, I really love how soft and sweet they are, especially when “forever” roasted (2½–3 hours). Does squash need to be roasted that long? Absolutely not, but isn’t it nice to cook something for the exact same time and at the exact same temperature as your turkey? I think so.

I know the squash, sage, and browned butter combination is giving “the ravioli special at the bad-but-good Italian restaurant” but damn, there is a reason it’s always the ravioli special. These three ingredients are perfect together, a true gift on your Thanksgiving table, especially for anyone looking for a casserole with marshmallows (“this is kind of like that!” you’ll say). The best part about this particular recipe is that you don’t have to brown the butter or crisp the sage. The butter browns and the sage crisps all on their own in the oven (they are in there forever, after all).

Ingredients (8)

Winter squash (acorn, butternut, honeynut, or kabocha)(3 lb, quartered lengthwise, seeds removed)
about 2 small
Olive oil(2 Tbsp)
Kosher salt
Black pepper(freshly ground)
Brown sugar(2 Tbsp)
divided
Unsalted butter(4 Tbsp)
Garlic(8 cloves, well smashed)
Fresh sage(½ bunch)
thyme, marjoram, or oregano also work

Instructions

Preheat oven to 275 °F. Place the squash (3 lb) in a roasting pan or baking dish.
whatever size accommodates, but a standard 2–3 quart should do the trick
Drizzle all over with olive oil (2 Tbsp), and season with salt and pepper.
Scatter the cut side of the squash with brown sugar (2 Tbsp), and flip the squash to make sure it's all skin side up.
Tuck the garlic (8 cloves) and sage (½ bunch) under and around the squash and top with butter (4 Tbsp).
Place in the oven (if you’re doing the turkey legs too, they go in at the same time). Roast, without touching or flipping or turning, until all the squash is impossibly tender (you can poke it, and it should feel like it’s about to collapse), 2 ½–3 hours (approximately forever). The garlic will be jammy, the sage will be crisp, the squash will be soft, you will be happy.
Serve the squash in or out of the skins (you can eat the skin!), scattered with the garlic, sage, and browned-butter-and-brown-sugar business that's pooled at the bottom of the dish.

Notes

Seeds

Usually when roasting squash, I leave the seeds in, but here, I find they don’t do as well getting roasted low and slow, so I remove them. That said, I do eat them, of course. Rinse them in cold water, letting any squashy bits float to the top, and remove. Drain the seeds, pat dry on a little paper towel, and toss with olive oil, salt, and pepper. Add some paprika or chili flakes if you want. Roast at 425°F, tossing occasionally, until they’re crisped and evenly golden brown, 20–25 minutes. I grew up doing this with my dad after we’d carved pumpkins, and now I do it with all my squash. Truly a wonderful crispy-salty snack.

Do ahead

You can prepare your squash whenever you want, really, no need to do it ahead. But if you do, just gently rewarm in the oven in the baking dish it’s roasted in.

Leftovers

There is nothing clever to do with this squash, but I like popping it back into a tiny skillet or baking dish and reheating in the oven so it regains some of its caramelization-crispy-bits stuff on the bottom. Probably also good in a microwave?

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