Roasted acorn squash crescents with a cranberry pear balsamic glaze and pecans on a cream platter

AmericanSide

Roasted Acorn Squash with Cranberry Pear Balsamic Glaze

Tender, caramelized crescents of roasted acorn squash with a glossy cranberry pear glaze, the easy Thanksgiving side that looks like you fussed. The squash roasts in Winter Herb Extra Virgin Olive Oil, our seasonal Signature Estate olive oil co-milled with fresh rosemary, sage, thyme and garlic, so the herbs are already in the oil. The glaze is Jeweled Cran-Pearberry Fruit Balsamic, a Greek fruit balsamic rested with cranberry and pear, simmered with a little maple syrup until syrupy. Tart cranberry, ripe pear and warm herbs land on every bite. Toasted pecans finish the platter. Five ingredients, no peeling, about 45 minutes.

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Servings

6

Prep Time

15 minutes

Cook Time

30 minutes

Calories

215

Author

Kristina DeRolf

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Ingredients

2 medium acorn squash (about 1 ½ pounds each)
3 tablespoons Winter Herb Extra Virgin Olive Oil, divided
¼ cup Jeweled Cran-Pearberry Fruit Balsamic
2 tablespoons pure maple syrup
½ cup pecan halves
¾ teaspoon kosher salt
¼ teaspoon freshly ground black pepper

Directions

Heat the oven to 425°F. Line a large rimmed sheet pan with parchment.
Cut each squash in half from stem to tip and scoop out the seeds. Lay the halves cut side down and slice into 1-inch-thick crescents, following the ridges. No need to peel; the skin softens as it roasts.
Toss the squash on the sheet pan with 2 tablespoons Winter Herb Extra Virgin Olive Oil, the salt and the pepper. Spread in a single layer.
Roast 15 minutes, flip each piece, then roast 12 to 15 minutes more, until fork-tender and browned at the edges.
While the squash roasts, toast the pecans in a dry small skillet over medium heat 3 to 4 minutes, shaking the pan, until fragrant. Transfer to a plate.
In the same skillet, bring the Jeweled Cran-Pearberry Fruit Balsamic and maple syrup to a simmer over medium-low heat. Simmer 3 to 5 minutes, until reduced by about half and it coats a spoon. It thickens more as it cools.
Arrange the squash on a platter. Drizzle with the glaze and the remaining 1 tablespoon Winter Herb Extra Virgin Olive Oil, scatter the pecans over the top and serve warm.

Article: Roasted Acorn Squash with Cranberry Pear Balsamic Glaze

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Roasted acorn squash crescents with cranberry pear balsamic glaze and pecans on a Thanksgiving table with Winter Herb Extra Virgin Olive Oil and Jeweled Cran-Pearberry Fruit Balsamic

Nov 5, 2026Holiday

Roasted Acorn Squash with Cranberry Pear Balsamic Glaze

Name: Roasted Acorn Squash with Cranberry Pear Balsamic Glaze
Prep time: 15 min
Cook time: 30 min
Total time: 45 min
Yield: 6
Cuisine: American
Ingredients: 2 medium acorn squash (about 1 ½ pounds each); 3 tablespoons Winter Herb Extra Virgin Olive Oil, divided; ¼ cup Jeweled Cran-Pearberry Fruit Balsamic; 2 tablespoons pure maple syrup; ½ cup pecan halves; ¾ teaspoon kosher salt; ¼ teaspoon freshly ground black pepper

The Thanksgiving table has room for one side that is bright, colorful and a little unexpected, and roasted acorn squash fits that spot. Sliced into crescents, it looks beautiful on a platter, and there is no peeling. The skin softens as it roasts.

The flavor comes from two bottles. Winter Herb Extra Virgin Olive Oil, our seasonal oil with rosemary, sage, thyme and garlic, roasts with the squash. Then Jeweled Cran-Pearberry Fruit Balsamic simmers with a little maple into a glossy glaze. Toasted pecans finish it.

Planning the Day
Roast the squash a day ahead and keep the glaze in the fridge for up to three days. On the day, rewarm the squash while the turkey rests, glaze it and add the pecans right before it goes to the table.

A Seasonal Pairing
Both bottles are made for this time of year, which also makes them an easy host gift to bring along.

Shop the bottles: Winter Herb Extra Virgin Olive Oil and Jeweled Cran-Pearberry Fruit Balsamic

Written by Kristina DeRolf

Kristina DeRolf, CRNA

Founder of The Outward Olive and a practicing nurse anesthetist since 2012. Kristina selects every olive oil and balsamic we carry and writes about olive oil, wellness, and gathering well.

More about Kristina