Roasted acorn squash becomes the perfect vessel for a savory-sweet filling of tart cranberries, toasted walnuts, and creamy melted Brie. Fragrant fennel adds a subtle anise note that balances the creamy cheese, while the squash's caramelized edges bring warmth and depth to every bite. Elegant enough for a holiday table, yet simple enough to not require the whole afternoon, this seasonal dish celebrates the best flavors of fall in one beautiful presentation.
Cranberry, Fennel, Walnut, and Brie Stuffed Acorn Squash
Serves 4
Squash Ingredients:
2 acorn squash, halved and seeds removed
2 tablespoons olive oil
sea salt
freshly ground pepper
Filling Ingredients:
1 tablespoon butter
1 small fennel bulb, finely diced (about 1 cup)
1 cup fresh cranberries
1/2 cup fresh orange juice, plus
1 tablespoon set aside
2 tablespoons maple syrup
1 teaspoon fresh thyme leaves
1/4 teaspoon cinnamon
Pinch of red pepper flakes
sea salt
freshly ground pepper
1 teaspoon cornstarch
1/2 cup chopped walnuts, toasted
4 oz Brie, rind removed, cubed
Directions:
1. Preheat the oven to 400 F. Brush the cut sides of the squash with olive oil and season with salt and the pepper. Place cut-side down on a parchment-lined baking sheet and roast for 35-45 minutes, or until fork tender.
2. While the squash roasts, melt the butter in a skillet over medium heat. Add the diced fennel and cook for 6-8 minutes until softened and lightly golden.
3. Stir in the cranberries, orange juice, maple syrup, thyme, cinnamon, red pepper flakes, salt, and pepper. Simmer for 8-10 minutes, stirring occasionally, until most of the cranberries have burst.
4. In the same skillet, stir togetherthe remaining tablespoon oforange juice with 1 teaspoon cornstarch. Stir to create a slurry.Add this to the fennel andcranberry mixture, and continueto simmer. Stir until the consistency becomes jammy. Taste andadd additional salt andpepper as needed.
5. Remove from heat and stir in the toasted walnuts. Let cool for 5 minutes, then gently fold in the cubes of Brie.
6. Turn the roasted squash halves cut-side up on the sheet pan. Divide the filling among the squash cavities and return to the oven for 5-7 minutes, or just until the Brie begins to soften.
7. Serve the squash warm garnished with a couple of sprigs of thyme and a few extra toasted walnuts.
HOSTING TIP! This recipe may be prepped ahead of time. Simply roast the acorn squash and prep the filling 2-3 days ahead of serving. Wrap and store the filling and squash separately. Assemble and bake when ready to enjoy!