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Sweet Squash Stuffed with Mushrooms, Greens and Cranberries

October 11, 2012

I’m going to overdose on orange squash this year.

Butternut, carnival, pumpkin. I’m eating it all with reckless abandon.

Around this time last year, my husband and I escaped to the Finger Lakes region of New York. While there we happened to dine at a famous restaurant called Moosewood. Moosewood showcases creative vegetarian food by cooking with what’s local, fresh, and in season. Neither of us are vegetarians but we were both blown away by our meal at Moosewood.

Who knew a vegetarian meal could be so amazingly memorable?

The first thing I did when I got home was make my own batch of Moosewood Ginger Orange Tea. The second thing I did was email the restaurant and request the recipe for the baked stuffed squash entree. I needed to eat it again. Sadly, a recipe was not available. (It was a one-day special so they didn’t have one written down.)

Ever since I’ve been tweaking my own version of stuffed baked squash. It starts with a sweet squash – like a carnival or dumpling squash – basted with a little maple syrup and roasted to bring out all of its flavors. Next comes a quick sautee of the filling, composed of all my favorite savory Fall flavors: mushrooms, greens, cranberries, onions, and pecans. Then you stuff that squash, top it with some sharp cheddar and bake until it’s warm and melty. And there you have it – a warm, comforting vegetarian meal that tastes like Fall.

Because the squash is baked separately it can be made ahead of time and rewarmed in the oven once stuffed, making this a good option for quick weeknight meals. And because the filling is pre-cooked, the possibilities for fillings are only limited by your palette. I’ve used dried cherries instead of cranberries in the past, and I think some salty spicy sausage would be a nice addition. If you ask me, the cute, pumpkin-like presentation makes it even suitable for serving to guests.

I think you can see now why I’ve been obsessing over this dish for a whole year!

Sweet Squash Stuffed with Mushrooms, Greens and Cranberries

Serves 2

You can use dried cranberries or dried cherries in this recipe, as well as swiss chard (ribs removed) or spinach. I used a mix of both. Keep in mind that spinach will likely wilt faster than swiss chard so you’ll want to cook it a little less. The bread crumbs are optional, but I find they add flavor by absorbing the cooking liquids and they help hold the filling together. Make sure you use real maple syrup, not pancake syrup! Squash can be baked up to 2 days ahead to save prep time (see directions below).


1 Sweet Dumpling, Celebration or Carnival squash
2 teaspoons real maple syrup
1 Tablespoon salted butter
1 Tablespoon olive oil
1/4 cup pecans, chopped
1/2 medium onion, diced
8 ounces baby portabella mushrooms, roughly chopped
1/4 cup dry white wine
1/4 cup dried cranberries or dried cherries
2 cups spinach or swiss chard (ribs removed), chopped
2 to 3 Tablespoons Panko bread crumbs (optional)
2 to 3 ounces sharp cheddar cheese, grated
kosher salt, to taste


Preheat oven to 350°F.

Using a sturdy knife, cut squash in half from stem to bottom. Scoop out seeds and pulp with a spoon and discard. Pierce inside of each squash half a few times with a fork. Baste the inside of each squash half with a teaspoon of real maple syrup. Place squash cut-side-up in a bake dish. Add a little bit of water to the bottom of the dish, cover with foil and bake at 350°F for about 1 hour, or until softened.

(To make ahead: at this point you can cool squash to room temperature, wrap in plastic wrap or foil and store in the fridge for up to 2 days. Let squash sit out at room temperature while you prepare the filling, then stuff and bake until warmed through.)

To make the filling, adjust oven to 375°F. Melt butter in a large skillet or saute pan over medium heat. Toast chopped pecans in butter until fragrant, 3-5 minutes. Remove from pan and set aside.

Add olive oil to the same saute pan. Add onion and cook until softened. Add mushrooms and cook until browned, about 4-6 minutes. Add white wine and continue cooking until reduced by half. Add in dried cranberries or cherries and greens. Cook just until greens are wilted. Stir in breadcrumbs (if needed) 1 tablespoon at a time until cooking liquid is absorbed. Season with salt to taste (start with a big pinch, add more if desired). Remove from heat. Fold in chopped pecans and half of the grated cheese. Stuff each half of prepared squash with filling. Sprinkle remaining cheese on top. Place squash halves on a baking sheet and bake uncovered at 375°F for 10-15 minutes, or until squash is heated through.

  1. October 11, 2012 9:50 am

    This looks really yummy, I can’t wait to try it!

  2. ModernAlice permalink
    October 11, 2012 1:47 pm

    This looks so delicious! I’ve had the moosewood cook book for years and wish they had included this amazing recipe in it!

  3. totesdelishy permalink
    October 11, 2012 1:56 pm

    My mom cooked for me as a kid out of the Moosewood Cookbook, and I only have good memories from it. So much so that as a child I didn’t realize I was eating vegetarian… The dried cranberries in this recipe sounds fantastic can’t wait to try it myself.

  4. October 11, 2012 6:15 pm

    Beautiful photos!

  5. October 11, 2012 6:50 pm

    I love the idea of adding sausage! I’ve given Moosewood cookbooks as gifts to so many of my vegetarian friends.

  6. petit4chocolatier permalink
    October 11, 2012 6:54 pm

    This looks so good! I just saw a similar recipe like this in the Publix Supermarket magazine and am really thinking now of attempting it. Your pictures make it look divine! I am so glad I saw this!

  7. A Dog With Fleas permalink
    October 11, 2012 9:01 pm

    This looks delicious will all my favorite flavors!! Can’t wait to try! Thanks for sharing.

  8. October 11, 2012 9:35 pm

    yum :)

  9. A Table in the Sun permalink
    October 12, 2012 6:49 am

    This recipe looks fabulous. And the photos…………pure genius in their simplicity.

  10. Homemade Stockholm permalink
    October 12, 2012 5:22 pm

    The squash is beutiful!!

  11. eyeluvfood permalink
    October 15, 2012 7:53 pm

    Awesome! Looks good

  12. October 16, 2012 3:18 pm

    Wow, I am blown away just looking at this! I cannot even imagine tasting it! Definitely saving this recipe! :)

  13. October 19, 2012 11:00 am

    How beautiful is this?! Such a festive, seasonal meal that has all of my favourite flavours. I love the use of Crimini mushrooms, they have such a wonderful flavour… I will be trying this one very soon!


  14. November 4, 2012 10:02 pm

    We guessed and added in the pecans at the end with the cheese… :) The kitchen smells great and we ate the last few bits of stuffing that didn’t fit and it was delicious!! Thanks for the recipe.

    • The Craving Chronicles permalink*
      November 4, 2012 10:32 pm

      Oops, thanks for pointing that out Andria – good guess! I’ve fixed the recipe now. I always eat the last few bites too. Glad you enjoyed it :)

  15. December 26, 2012 11:16 am

    This food is gorgeous – I have never thought to stuff a squash. Silly me! I will be trying this soon, thanks for the post!

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