Challah stuffing stuffed acorn squash

Mushroom, Onion, and Challah-Stuffed Acorn Squash

Thanksgiving is one of my family’s favorite holidays. Besides Passover, it is one of the only times we all come together during the year and so my mother and I get pretty excited about planning; we spend months working on the perfect place cards, décor, side dishes and desserts. We went all out for Thanksgivukkah last year creating this recipe for sweet potato latkes with toasted marshmallows.

This year we are very much in the midst of menu planning, and can’t wait to make this new dish for challah stuffing stuffed acorn squash, made with classic Thanksgiving flavors like squash, dried cranberries, thyme and even pecans.

Challah stuffing stuffed acorn squash

This dish has a great “wow factor” due to its eye-catching presentation but is quite simple to make. You can even make it ahead of time to save time the day of Thanksgiving. This dish also serves as a great vegetarian entree for your guests.

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4 acorn squashes

½ leftover challah loaf (about 2 cups cubed)

1 yellow onion, chopped

3 cloves garlic, minced

8 ounces white mushrooms, chopped

2 tsp dried thyme

2 Tbsp soy sauce

½ cup toasted pecans, chopped

½ cup dried cranberries

½ cup to 3/4 cup vegetable or chicken broth, as needed

Salt & pepper to taste

Olive oil


Preheat oven to 350°F. Place parchment paper on a baking sheet and set aside.

Cut challah into ½ inch cubes and place on the baking sheet. Drizzle with olive oil and use your hands to toss the challah pieces and distribute the oil evenly. Toast in the oven for 15-20 minutes, tossing once halfway through. Set the toasted challah cubes aside.

Cut 3/4 inch off the top of each acorn squash and carefully scoop out the seeds and strings of each squash. Cut a sliver off the bottom of each squash and place them on the baking sheet. Drizzle with olive oil, generously season with salt and pepper, and replace the top of each squash, leaving room for steam to escape. Bake for 40 minutes.

Heat olive oil in a pan over medium-heat heat and sauté the diced onion until translucent. Add the mushrooms and thyme, stirring until the mushrooms brown. Add garlic.

Once no liquid is left in the pan, deglaze the pan with soy sauce. Add cranberries, pecans, challah and vegetable broth, stirring until the vegetable broth is absorbed and the mixture starts to come together. You can add additional broth if the mixture is too dry to come together. Add salt and pepper as needed.

Stuff the squash with the challah mixture until slightly mounded. Place the top of each squash next to its body. Bake the squash and stuffing for 25-30 minutes, until the stuffing is lightly browned and the flesh of the squash can be pierced easily with a fork. Place the top of each squash on top of the stuffing to serve.

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