Maple Roasted Acorn Squash Stuffed with Wild Rice Pilaf

The cut sides of the squash come out of the first roast softened, but not yet ready to eat. That’s the moment to turn them over and brush on the…

By Willow • October 25, 2026 • Reading time: 9 min

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The cut sides of the squash come out of the first roast softened, but not yet ready to eat. That’s the moment to turn them over and brush on the maple syrup, so it coats the flesh for the final stretch in the oven instead of sitting against the pan. I like this two-part approach for Maple Roasted Acorn Squash Stuffed with Wild Rice Pilaf because the squash gets tender while the maple finish stays right where you want it.

The wild rice brings a pleasantly chewy texture that holds up inside the squash, while dried cranberries add a little tartness and pecans bring crunch. Since the rice takes longer to cook than the squash, I start the pilaf first and keep it covered while the squash roasts. By the time the squash halves are ready, the filling is warm, fragrant, and easy to spoon in.

The Maple Goes on After the First Roast for a Reason

Maple syrup has natural sugars that can darken during roasting. Brush it onto raw squash and it spends the whole time in the oven against the hot pan, which makes it easier for the surface to get too dark before the flesh turns tender. Here, the first roast gives the cut sides a head start. Turning the halves cut side up before adding maple lets the syrup coat the exposed flesh for the shorter finish.

That order also keeps the squash’s own juices from washing the maple off as it softens. Look for a thin, even coating rather than a puddle in each cavity; the syrup should cling to the surface and turn glossy in the final stretch. It’s a small timing choice, but it gives you tender squash with a clear maple note instead of a burnt-sugar edge.

The Ingredients That Keep the Filling Chewy, Bright, and Balanced

• Wild rice — Its firm, earthy chew stands up to the soft squash instead of disappearing into it. Rinse and drain it before cooking, and use actual wild rice rather than a quick-cooking rice blend; the grains and simmer time won’t match.
• Low-sodium vegetable broth — It seasons the rice as it cooks without making the finished pilaf too salty. Low-sodium broth gives you more control, especially since the rice reduces as it simmers.
• Onion, celery, and garlic — These form the savory base that keeps the filling from tasting sweet all the way through. Finely chopping the onion and celery helps them soften in the short sauté before the rice goes in.
• Dried cranberries, pecans, and parsley — Cranberries bring tartness, pecans add a crisp bite, and fresh parsley keeps the final spoonful lively. Chop the pecans so they distribute through the pilaf rather than landing in a few large pieces.
• Acorn squash and pure maple syrup — Medium acorn squash halves make sturdy individual vessels, and pure maple syrup gives the roasted surface a woodsy sweetness. Maple syrup is worth choosing over pancake syrup here; the two don’t have the same flavor or finish.

How to Cook the Pilaf Before the Squash Is Filled

Soften the Aromatics, Then Simmer the Rice

Melt the butter in a medium saucepan over medium heat, then add the finely chopped onion and celery. Stir occasionally for 4–5 minutes, until they’ve softened without taking on much color. Stir in the minced garlic for 30 seconds, then add the rinsed wild rice, vegetable broth, and kosher salt. Bring everything to a boil, cover, reduce the heat to low, and simmer for 45–55 minutes, until the grains split and are tender but still chewy.

Finish the Pilaf While It’s Hot

If broth remains once the grains are tender, drain the excess so the filling won’t be wet. Stir in the dried cranberries, cover, and let the saucepan stand off the heat for 5 minutes. Fold in the chopped pecans and parsley, then cover the pilaf again while the squash roasts. The cranberries soften in the covered rest, and the pecans and parsley go in after that so their textures stay distinct.

Start the Squash Cut Side Down

Heat the oven to 400°F and line a rimmed baking sheet with parchment paper. Cut each acorn squash in half lengthwise and scoop out the seeds, then rub the cut sides with olive oil and sprinkle them with black pepper. Arrange the halves cut side down on the lined sheet and roast for 25–30 minutes. At this point the flesh should be starting to soften, not yet fork-tender.

Brush with Maple and Fill the Tender Halves

Turn the squash halves cut side up and brush the cut surfaces with pure maple syrup. Return them to the oven for 15–20 minutes, until a fork passes through the flesh easily. Transfer the pilaf to a microwave-safe bowl, cover, and microwave for 2–3 minutes, stirring once, until steaming hot. Spoon the warm pilaf into the squash halves and serve.

Three Ways to Adapt the Squash-and-Pilaf Format

Questions That Come Up While the Squash Roasts

Maple Roasted Acorn Squash Stuffed with Wild Rice Pilaf

Maple roasted acorn squash stuffed with wild rice pilaf pairs fork-tender squash with chewy wild rice, cranberries, and pecans. Roast the squash cut side down first, then brush it with maple syrup for a sweet, caramelized finish.

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Prep Time 20 minutes mins

Cook Time 1 hour hr 43 minutes mins

Standing time 5 minutes mins

Total Time 2 hours hrs 8 minutes mins

Servings: 4 servings

Course: Side Dish

Cuisine: American

Calories: 430

Ingredients Equipment Method Notes

Ingredients

  

For the wild rice pilaf

• 2 tbsp unsalted butter
• 0.5 cup yellow onion finely chopped
• 0.5 cup celery finely chopped
• 2 cloves garlic minced
• 1 cup wild rice rinsed and drained
• 3 cups low-sodium vegetable broth
• 0.75 tsp kosher salt
• 0.33 cup dried cranberries
• 0.33 cup pecans chopped
• 2 tbsp parsley fresh, chopped

For the squash

• 2 acorn squash medium
• 1 tbsp olive oil
• 0.25 tsp black pepper
• 2 tbsp maple syrup pure

Equipment

• 1 rimmed baking sheet
• 1 microwave

Method

 

Make the wild rice pilaf

1. Melt the butter in a medium saucepan over medium heat.
2. Add the onion and celery and cook, stirring occasionally, for 4–5 minutes until softened.
3. Stir in the garlic and cook for 30 seconds.
4. Add the wild rice, broth, and kosher salt.
5. Bring the mixture to a boil.
6. Cover, reduce the heat to low, and simmer for 45–55 minutes until the grains split and are tender but still chewy.
7. Drain any excess broth.
8. Stir in the cranberries, cover, and let stand off the heat for 5 minutes.
9. Fold in the pecans and parsley.
10. Cover the pilaf while you roast the squash.

Roast and fill the squash

1. Preheat the oven to 400°F and line a rimmed baking sheet with parchment paper.
2. Cut each squash in half lengthwise and scoop out the seeds.
3. Rub the cut sides with olive oil and sprinkle with black pepper.
4. Arrange the squash cut side down on the baking sheet and roast for 25–30 minutes, until the flesh is starting to soften.
5. Turn the squash cut side up and brush the cut surfaces with maple syrup.
6. Roast for 15–20 minutes more, until fork-tender.
7. Transfer the pilaf to a microwave-safe bowl, cover, and microwave for 2–3 minutes, stirring once, until steaming hot.
8. Spoon the pilaf into the squash halves and serve.

Notes

For evenly tender squash, choose halves of similar size and check for fork-tenderness before filling. Refrigerate leftovers in an airtight container for up to 4 days; freezing is not recommended because the squash softens. For a dairy-free version, replace the butter with olive oil.