A Smitten Kitchen hack will smash your squash anxiety (and result in cheesy, spicy goodness)

It was a vibrant autumn afternoon, in one of my favorite eateries. I was seated at Woodstock’s Dixon Roadside, the cozy yet modern restaurant from the same folks behind Phoenicia Diner, drinking pinot out of a can and feeling all was right with the world. Best of all, I was eating exactly the kind of thing I’d never make for myself at home — a generous portion of ancho roasted butternut squash. It was insanely good, a dish I’d gladly eat weekly. But I have squash obstacles. 

Squash is undoubtedly one of the best things about the fall, but I always recoil from actually buying them, because then I’d have to cut into them. Give me a can of pumpkin puree and I’m golden. Give me some of the pre-cut stuff at the supermarket, and sure, maybe I’ll give it a sniff. Show me a whole butternut or a kabocha or an acorn and I’m like, “What is this, the safe at the Bellagio?” 

Perhaps you too struggle with squash anxiety. Maybe you’ve ineptly thrown your full weight on a delicata only to have it skitter away from you down the counter. Maybe you just don’t want this to be the way you lose a finger today.

Luckily for me, however, I recently interviewed Smitten Kitchen’s Deb Perleman, and happened to mention to her my terror of squash cutting. “It’s scary,” she concurred. But then she, in her encouraging Smitten Kitchen way, offered some advice. “Always cut against a flat surface,” she said. “Don’t try to cut into a soccer ball. Cut a little edge off the bottom, get it solid on the surface, and then you can really push down on the knife.” And let me tell you, I went right out and bought a damn squash.


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Some people peel their squash, but I think slicing it is enough of a challenge for one day. My Dixon Roadside squash was roasted with ancho, but my spice rack has chipotle powder so that’s what I used. And because I wanted a squash that was a little tangy and sweet, I used brown sugar and vinegar for balance. Then, just to push the whole thing to another level, I topped it with some grated parmesan cheese and roasted pepitas. Boom, suddenly I had a squash. A really, really good squash.

This is a squash that says, “I am not a side dish.” Nobody puts this squash in a corner. It is hearty and substantial and a little dramatic, even. It’s also hands-off enough to slide into your weeknight repertoire like it’s no big deal at all. The hardest part is just cutting the thing in half — and it turns out that’s so hard at all either.

* * *

Inspired by  The Fig Jar and Dixon Roadside

Spicy Roasted Butternut Squash

Yields

 2 servings

Prep Time

 10 minutes

Cook Time

 60 minutes

Ingredients

  • 1 butternut squash 
  • 2 tablespoons of olive oil
  • 1/4 cup of brown sugar
  • 2 teaspoons of ground chipotle 
  • 1 tablespoon of apple cider vinegar 
  • 2 tablespoons of grated parmesan or romano cheese
  • Optional: 2 tablespoons of pepitas 
  • Salt and pepper to taste

Directions

  1. Preheat your oven to 400 degrees. Line a sheet pan with parchment.
  2. With a sharp knife, slice a little bit off the bottom and top of the squash. Turn it on to a level surface and slice lengthwise. Take your time. Scoop out the seeds.
  3. In a small bowl, stir together the olive oil, brown sugar, ground chipotle and vinegar.
  4. Lightly score the squash halves with a few shallow cuts, then brush or spoon your olive oil mixture evenly over both.
  5. Roast cut side up on your sheet pans for roughly one hour, until very burnished and tender.
  6. Top with cheese and pepitas, and salt and pepper. Serve immediately, with hot sauce on the table for extra kick.

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