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This squash dish is a new Thanksgiving tradition in our family. I created it last fall after being asked to bring an orange vegetable side to dinner at a mushroom-lover’s house. It seemed to hit every note I wanted: easy to prepare, accessible ingredients, festive and pretty on the table. The primary flavors in the stuffing– sweet leeks, hearty mushrooms, familiar sage– are all good matches for squash, and they provide textures and colors that are wonderful to taste and see. I used Kabocha squash last year and have experimented with Butternut, acorn and blue Hubbard as well. For Thanksgiving this year, I’m trying a new-to-me variety called Butterkin, because of its low, bowl shape and promised creamy and sweet flavor profile. I’d say you could pretty safely try any kind of winter squash you enjoy (maybe not spaghetti squash because of the texture) and have this stuffed squash recipe turn out beautifully.

If you’re looking for a hearty meal, more of an entree than a side, I’ve also made this with cooked wild rice mixed into the leek mixture, served as an adorable one-squash-per-guest meal. I crumbled bacon over the top when I made it with acorn squash, and it was salty and crunchy and good. I have also tried using a tart apple in place of dried cranberries: I diced a Honeycrisp apple and added it to the stuffing after the mushrooms had cooked, just before filling the squash halves, so it stayed a little crunchy. Honestly though, the mix of leeks and different mushrooms in a buttery sauce feels decadent without any additions. You could add other vegetables to the stuffing, or make the other changes I mentioned, but “plain” is pretty darn good as is.

It feels nice to add some new sides to our rotation of holiday favorites, and at the same time, to make a squash dish that tastes great every day of the year. Please comment: what’s your favorite squash dish to make? Do you have a traditional side you’re looking forward to on your holiday menu? I’d like to wish you all a safe and happy Thanksgiving– I certainly think of your continued readership and support when I think of all I have to be thankful for each year. Cheers!

Mushroom & Leek Stuffed Squash

Mushroom & Leek Stuffed Squash (serves 2-4 as entree, 6-10 as side)

  • 1 medium-sized winter squash, cut in half around the center to form two bowls, seeds removed
  • 2 T. olive oil, plus extra for the squash
  • 4 T. unsalted butter, divided
  • 2 – 2 1/2 c. thinly sliced leeks, white and light green parts only, from 1 large or 2 medium leeks
  • 8 oz. chanterelle mushrooms, cleaned thoroughly and roughly chopped*
  • 8 oz. white button or cremini mushrooms, cleaned and sliced
  • 1 tsp. dried sage, crumbled
  • 1/2 tsp. dried thyme, crumbled
  • 1/2 c. vegetable or chicken broth
  • 1/4 c. dried cranberries, or dried tart cherries
  • salt & pepper to season

Preheat the oven to 375 degrees. Place the squash halves, cut side down, on a lightly greased cookie sheet or baking pan. You can cover the pan in parchment or tin foil to assist with clean-up; if you plan to do so, lightly oil the edge of each squash half so it doesn’t get stuck on the pan.

Bake for 20 mins., then carefully turn each squash over on the pan. Season the center with salt and pepper and cook for another 15-20 mins. When tested, the squash should be firm, but with enough give that you can pierce it with a fork. At this point, you can pause for up to 2 days by cooling the squash to room temperature and carefully wrapping it to store in the refrigerator.

On the day you plan to serve, if you refrigerated the par-cooked squash, remove it and let it come up to room temperature (or close) while you make the stuffing.

Preheat the oven to 350 degrees. Lightly oil a baking dish that fits the two squash halves snugly side by side, but allows them to lie flat. If you don’t have the right size baking dish to fit both, put each squash half in its own dish. Pie plates work well here.

Place a large skillet over medium heat and add 2 T. olive oil and 2 T. butter. When the butter has melted, add the leeks to the pan and cook for 5 mins. Add both kinds of mushrooms and cook for about 3 mins., until they begin to soften. Season with salt and pepper. Stir in the sage and thyme, then add the stock and dried cranberries. Reduce the heat to medium and cook for just another 2-3 mins. Remember that the stuffing will cook further in the oven, so it’s okay if the vegetables are al dente. Divide the filling between the two squash halves and dot the top of each with 1 T. butter. Bake for 20-25 mins. The dish is done when the edges of the squash are fork-tender.

Remove whole to a serving dish for a family-style table setting or, as an entree, serve each guest one, or half of one, squash half. For an easier but less dramatic presentation, scoop out the squash into a serving bowl with stuffing mixed in or on top of the bowl.

*If you have trouble finding chanterelles, substitute an equal amount of another wild mushroom you like, or double the amount of white button or creminis you’re using.

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