Stuffed Squash with Brie, Cranberries and Greens

Fresh cranberries, brie and greens come together to make a festive and flavorful filling for kabocha or acorn squash.

The cranberries add a tangy pop of sweetness to the gooey brie, tender greens and mild-mannered squash.

The best bite is when you dig deep and not only get the creamy greens but some of the dense squash on your fork too! The difference in textures is just as important as the flavors in making this surprisingly delicious.

With it’s pretty red and green colors combined with seasonal flavors, this just begs to be on your holiday table. If allowed, it sidles right in and promises to become a tradition. But I’m not condoning waiting until then to make it! Tis’ the season of squash and cranberries! Take advantage and enjoy them every chance you get.

I used swiss chard because that’s what I’m in love with at the moment – use any greens you like. Substitute dried cranberries for fresh and if you don’t like brie use whatever melting cheese you do like – swiss, fontina or mozzarella would be wonderful.

This is my entry for Side Dish Saturdays, a weekly event I started to bring more attention to side dishes and give them the respect and love they deserve.

I would love it if you linked up your side dishes! I only have two guidelines for linking to the event.

Your link must be a side dish; no soups or recipes with meat/poultry. Old posts are ok but. . .

The post must have a link back to my site. All other links will be deleted; every link will be checked.

The linky will be open until Monday at midnight eastern time. If you get here late – no worries – just link up next week.

Stuffed Squash with Brie, Cranberries and Greens

Rating: 51

Prep Time: 20 minutes

Cook Time: 45 minutes

Total Time: 1 hour, 5 minutes

Yield: 8 servings

Stuffed Squash with Brie, Cranberries and Greens

Fresh cranberries, brie and greens come together to make a festive and flavorful filling for kabocha or acorn squash.


2 small kabocha or acorn squash
olive oil, for drizzling and sauteing
sea or kosher salt and fresh black pepper
1 tablespoon butter
4 cloves garlic, minced
1 cup fresh cranberries or 1/2 cup dried
10-12 cups swiss chard, kale or spinach, rough-chopped (washed and dried, stems removed)
7-8 ounces brie, cut into bite-size pieces
1-2 tablespoons panko or seasoned bread crumbs


  1. Preheat oven to 400 degrees F. Cut both squash in half, scoop out seeds and trim bottoms if needed so they stand up evenly. Drizzle oil lightly over tops and sprinkle with salt and pepper. Roast 25 minutes.
  2. Meanwhile in a large skillet melt butter and a tablespoon of oil over low heat; add garlic and cranberries; saute until cranberries soften. Add greens and saute until wilted. Season with salt and pepper. Mix in brie, when it starts to melt remove from heat.
  3. Divide the greens evenly among the squash; sprinkle tops with bread crumbs. Bake an additional 20 minutes or until squash is tender. Cut each squash half into quarters for serving.

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  1. Lyndsey@TheTinySkillet says

    OMG I want to dive right in to this side dish! I love the way it looks with all the colors! Mmmmm….

  2. teresa says

    oh my goodness, i’ll take the whole thing, thank you!  this looks so good, adn i love all the colors!

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