topsy turvy stuffed squash

Every year, our referral logs show that visitors arrive at macbebekin searching for vegetarian-friendly Thanksgiving dishes. (And sometimes not-so-vegetarian-friendly Thanksgiving searches end up here, too.) Last year, I jotted down some tips and suggestions for a vegetarian-friendly holiday table, and in the same entry I outlined our proposed Thanksgiving menu, which centered around The Fella’s gorgeous roasted butternut squash galettes.

This year, I have one more vegetarian Thanksgiving entree to suggest, and boy howdy, it’s a doozy! Inspired by The Kitchn’s rendition of Dorie Greenspan’s stuffed squash, I whipped up a vegetarian version of my own. You’ll notice that the recipe at the link includes bacon, but don’t get hung up on that: the key here is the technique, not the ingredients.

I’ve never been a fan of baked stuffed squash, which too often comes out of the oven pallid and limp, slumping and drooling its thin juices onto the plate. But this simple, brilliant idea turns that bland, pale stuffed squash on its head — literally. The trick: hollow out the squash and fill it with cheesy, bready, aromatic stuffing…

And then flip it upside-down to bake.

Elsa's topsy turvy stuffed squash

It’s so simple and so obvious: get the stuffing in contact with the pan, let the oven’s heat and the roasting pan’s surface work their alchemy upon the ingredients. Here’s a photo of the squash halves, one still resting in the pan, the other flipped up to show off the crispy underside. As you can see, cooking them face-down results in tender roasted squash with a deeply browned, richly crisped crust over creamy soft stuffing.

The fabulous contrast in textures and flavors makes this a dish you’ll groan over. Our dinnertime last night was a chorus of “OOOOOH”s and “AAAAAAH”s and other, less polite expressions of delight. I urge you, urge you, to try this topsy-turvy stuffed squash soon.

note: even as I ate my delicious squash, I took mental notes and made plans to revise the recipe further; the squash you see in the photo was made with the recipe I’m giving here. I’ll appending my tasting notes and suggestions for proposed future versions at the end.

topsy turvy stuffed squash

1 acorn squash, scrubbed, split, and seeded
1 1/2 cups cubed or torn bread, stale or slightly dried in oven
1 onion, diced or slivered
2 cloves garlic, slivered
1 cup mushrooms, sliced
3/4 cup mixed cheese (I used mostly Swiss with a scattering of provolone and mozzarella)
1/3 cup sherry
3-4 TBS cream
3-4 leaves of sage
sprinkling each of rosemary, chili powder, freshly grated nutmeg
butter or oil
salt and pepper

Preheat oven to 400F. Select a nice heavy roasting pan that can easily accommodate the squash halves laying face-down. Earthenware, oven-safe glass, or enameled cast iron would be ideal.

Heat a splash of oil or sliver of butter in a saute pan and add onions, garlic, sherry, and a generous sprinkling of salt. Cook over medium heat until onions are tender and gently browned and liquid has cooked off. Add mushrooms and seasonings, raise heat to medium-high. Saute until rich brown. Remove from heat and cool slightly.

Right in the pan, toss onion-mushroom mixture with bread cubes, cheese, and cream. Taste mixture and add salt & pepper as desired; the stuffing should be highly seasoned.

Rub squash halves with a small splash of oil, then salt and pepper them inside and out. Spoon stuffing into squash halves, packing it well so they can lie face-down and flat in the pan. (Notice that I overstuffed the squash, to no ill effect. If you prefer a tidier presentation, just barely fill the squash and allow its cut surface to make contact with the roasting pan. Any extra stuffing will be delicious cooked in a ramekin.)

Place face-down in the ungreased pan and bake at 400 until squash is tender when pierced with a knife, 45-60 minutes for a hard acorn squash. Let rest five minutes and serve.

We had our squash with a side of broccoli; something fresh and green makes a good foil to the rich, savory flavors of the stuffed squash.

notes: This technique is a winner, and the recipe itself is fantastic… but I’m going to try ringing a few changes on it in the future. If I use an acorn squash again next time, I’ll roast it at a lower temperature, which should allow the squash to cook through while the stuffing crusts up more delicately and less thoroughly than ours did last night. Or perhaps I’ll try stuffing a delicata squash at the prescribed 400F. With its tender skin and thin flesh, a delicata should cook through faster at the higher temp.

This creamy, cheesy stuffing is very rich, suitable for a holiday table but not for every day. Next time, I’ll cut down the cheese to 1/2 cup, replace the cream with vegetable stock or milk (both of which we keep around the house; holiday pie-baking time is the only time I’m likely to keep cream in the house).

Best of all, I’m going to try making stuffing with whatever leftover vegetables, cheeses, and herbs we have in the fridge. This recipe will lend itself to improvisation all winter long!

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