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Gluten-Free Stuffed Acorn Squash with Cranberry Glaze
Original recipe: 4 servings · Prep: 20 min · Cook: 45 min · Total: 65 min
By Freeflourish Editorial TeamPublished May 11, 2026 | Updated Oct 20, 2026
American-inspired
65 mins
glutenfreedairyfreefamilyfriendlyholidayclassicsidedishmaincourse
Four roasted acorn squash halves hold a pumpkin, sage and cooked wild-rice filling, finished with cranberry glaze. Allow an estimated 65 minutes, including up to 35 minutes roasting and a further 10-minute bake. Start with cooked wild rice; cooking the rice takes additional time.
Prep
20 min
Cook
45 min
Total
65 min
Servings
4
Difficulty
medium
Cuisine
American-inspired
Ingredients
Servings
4
- 2 medium acorn squashes, halved and seeded
- 2 tablespoons olive oil, divided
- Salt and freshly ground black pepper, to taste
- 1 cup pumpkin puree
- 1 small yellow onion, finely chopped
- 2 cloves garlic, minced
- 1 cup cooked wild rice
- 2 tablespoons fresh sage, finely chopped
- 1/4 cup pecans, chopped (optional)
- 1/2 teaspoon ground cinnamon
- 1/4 teaspoon ground nutmeg
- 1/4 teaspoon smoked paprika
- 1 cup fresh or frozen cranberries
- 1/4 cup pure maple syrup
- 1 tablespoon balsamic vinegar
- 1/4 cup water
- Fresh sage leaves, for garnish
Instructions
-
Preheat your oven to 400 degrees F.
-
Brush the acorn squash halves with 1 tablespoon olive oil and season with salt and pepper. Place cut side down on a baking sheet lined with parchment paper.
-
Roast the acorn squash for 30-35 minutes, or until tender when pierced with a fork. Remove from the oven and let cool slightly.
-
While the squash roasts, heat the remaining 1 tablespoon olive oil in a skillet over medium heat.
-
Add the chopped onion and sauté for 5 minutes or until translucent. Stir in the garlic and cook for another 1 minute until fragrant.
-
In a large bowl, combine the pumpkin puree, sautéed onion and garlic, cooked wild rice, chopped sage, pecans (if using), cinnamon, nutmeg, smoked paprika, and season with salt and pepper to taste.
-
In a small saucepan, combine cranberries, maple syrup, balsamic vinegar, and water over medium heat.
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Bring the cranberry mixture to a boil, then reduce heat and simmer for 10 minutes, or until the cranberries burst and the sauce thickens slightly. Remove from heat and set aside.
-
Fill each roasted acorn squash half generously with the pumpkin and sage stuffing mixture.
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Return the stuffed squash halves to the oven and bake for an additional 10 minutes to warm through and meld flavors.
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Drizzle the cranberry glaze over each stuffed squash before serving.
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Garnish with fresh sage leaves and serve warm as a holiday main course or side dish.
Tips
Start with cooked wild rice. While the squash roasts, prepare the filling and cranberry glaze. Add the glaze after the filled squash has had its final bake. Pecans are optional; check all ingredient labels for individual allergy needs. Check that packaged ingredients are labeled gluten-free, and keep preparation surfaces and utensils free from gluten cross-contact.
More gluten-free squash recipes
For another squash-and-sage dinner, try roasted butternut squash and sage risotto.
For a different filling, follow the separate recipe for lentil and quinoa stuffed acorn squash.
Frequently Asked Questions
- Is the rice cooked before mixing?
- Yes. Measure one cup of cooked wild rice for the filling. Cooking the rice is additional preparation.
- How many filled squash halves does this make?
- Two acorn squashes make four filled halves.
- How do I keep the recipe gluten-free?
- Check that packaged ingredients are labeled gluten-free, and keep preparation surfaces and utensils free from gluten cross-contact.
Storage
Refrigerate leftovers promptly in covered containers for up to 4 days. Reheat to 165°F (74°C).
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