How to caramelize winter squash

Is it just me, or do you have an idealized notion about what winter squash should taste like too? I always, and I mean always expect it to taste like kaddo from The Helmand in Cambridge (which I found out recently is made of pumpkin baked in literal heaps of sugar). But then I go to the store, buy an acorn squash or something, bake it and am surprised to find it taste more like dirt than sugar. Every damn Fall.

The bad news is: the flavor of a winter squash is never going to live up to the romanticized version of it in your mind without the aide of heaps of sugar.
The good news is: there are certain techniques you can use to coax the natural sugars out of a pumpkin and get it tasting less like dirt and more like a vegetable you don’t resent.

  1. Start with a low-moisture and/or high sugar variety.
    My personal favorite is the red kuri squash, which is known for it’s dense texture and nutty flavor. You may have more luck finding one of those crazy cute and increasingly popular honeynut squash at a store like Trader Joe’s. At the farmer’s market, keep an eye out for blue hubbards, kabocha squash and peanut pumpkins (the more warts the better!). Delicata are delicious and easy to work with, but they’re actually in the same family as summer squash/zucchini and their flavor shows it. They lack that deep, rounded sweetness of a true winter squash.

  2. Old pumpkins are good pumpkins!
    In case you’ve missed one of the 200 times I’ve talked (bragged) about it, Eivind grew all the red kuri squash I’m working with this year. And one of the first things I learned about pumpkins is: they’re not good right after they’re picked! The sugars are not fully developed and they tend to be overly fibrous. Don’t be surprised if you buy two squash at the same time, roast one right away and find that the second one becomes much more caramelized when you bake it two weeks later.

  3. Use a sturdy, flat baking sheet and don’t crowd the pan.
    Surface area is key to caramelization. All the color that will develop on the flat sides of the squash will come from contact with the hot pan. It’s important that the pan sits evenly and holds heat evenly. You will still get decent color if you line the pan with parchment paper or a silpat, but the best color comes from direct squash to pan action.

  4. Put the pan in the oven while it preheats.
    This both helps the squash begin caramelizing instantly when it hits the hot pan and keeps it from sticking.

  5. Slice no thinner than 1”.
    To really have time to caramelize, you will need to bake your squash for at least 40 minutes at 400 to 425 degrees. I find that 1” slices cook through just the right amount in the time it takes for them to also get golden brown.

  6. Salt at the last minute!
    Liquid is the enemy of caramelization and if you salt any vegetable and let it sit even for five minutes, it will begin to draw out water. So here’s how this is going to play out:
    -peel your pumpkin if it’s bigger than a melon or exceptionally warty. scoop out the seeds and slice it into 1” pieces.
    -preheat the oven (with the pan inside) to 400 if your oven is reliable or up to 425 if it is not
    -when the oven come to temp, toss squash with olive oil and plenty of salt
    -turn it out onto the hot pan, making sure the cut sides are laying flat. add another drizzle of olive oil for good measure.
    -bake 20 minutes, flip, then bake 20 more minutes or until soft and golden. the cooking time will vary between squash, but generally speaking, the smaller and softer the squash, the faster it will cook. A honeynut, for example, can be halved and baked cut side-down in 20-30 minutes.