Winter squash agrodolce with cranberries will bring festive color and Italian flavors to your table. The squash roasts on a sheet pan while you make the simple sauce, and everything is ready in about 30 minutes!
Agrodolce is a classic Italian condiment, or sauce if you will, that means sour and sweet, made with vinegar and sugar, or honey, or maple syrup for the base flavors. Then you can add various herbs, aromatics, nuts, fruits, etc. according to your whims and what's in season.
If you know me at all you know I lovelovelove vinegar in everything! This sweet-sour concoction with its savory elements of garlic and sage has a tangy, bright finish. I promise it will open up your mind to what a sauce can be and it uses mostly pantry ingredients!
You can make agrodolce with endless combinations of types of vinegar and sweeteners. For this recipe we're using honey because the natural sweetness goes so well with the roasted squash, and red wine vinegar for its festive color that complements the cranberries!
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Winter Squash Agrodolce Ingredients
- Acorn and delicata squash: This is a lovely combination of types of winter squash to use because neither require peeling, they cook at about the same rate, and they are so pretty! Look for squash that are heavy for their size without any soft spots. Do not use kabocha squash, I tested it and it gets too dry when roasted and won't have the right texture.
- Red wine vinegar and honey: These two ingredients make up the agrodolce of it all, the sweet and sour.
- Sage, shallots, garlic: We need some savory to balance the tanginess, and to keep the agrodolce from going too far into sweet territory. I tested the recipe with various combinations of herbs and aromatics, and this combo was the absolute winner! Who doesn't want sage in a Thanksgiving or Christmas side dish?
- Dried cranberries: We love to use dried cranberries in a salad, but these are not going to stay dried. They'll plump up and absorb some of the sauce for little pops of sweetness in every bite, while adding festive holiday flavors!
- Chopped hazelnuts: We need a little texture because the squash is soft, so chopped hazelnuts will do that and still keep it Italian. If you can't find them, try walnuts or pecans instead.
*Ingredients with measurements are listed in the recipe card below.
How to make winter squash agrodolce
Step 1: Slice the squash
Use a good chef's knife to cut the ends off the delicata squash, stand it on one end, then slice it in half. Scoop out the seeds and slice in to half circles that are about ½" thick.
To cut the acorn squash, lay it on its side and carefully cut off the stem end. Then stand it up on the cut side, cut in half and scoop the seeds out. You can cut it into half circles or slice lengthwise along the ridges.
Step 2: Roast the squash
Preheat the oven to 425°F. Place the racks in the upper and lower third of the oven. Separate each type of squash on two separate sheet pans, drizzle with olive oil, season with kosher salt, toss to coat.
Bake for 15 minutes, then remove the sheet pans and flip the squash pieces over. Return to the oven, placing the pan that had been on the top rack on the lower rack and vice versa. Bake for another 5-15 minutes until golden brown and soft, transfer to a serving plate.
Step 3: Make the agrodolce sauce
Meanwhile, make the cranberry agrodolce sauce. Mince the shallot and chop the sage finely, then use a microplane grater to grate the garlic.
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Place a medium skillet over medium heat. Add the olive oil and once shimmering, add the shallots and a small pinch of kosher salt. Cook, stirring frequently until soft and translucent, 3-5 minutes. Add the garlic and sage and stir constantly for 30 seconds to 1 minute.
Add the vinegar, honey, and cranberries and bring to a simmer, reduce heat to low and cook, stirring occasionally, until sauce is reduced by about ⅓ and is thick enough to coat the back of a spoon. It should still pour easily.
Step 4: Finish and serve
Pour the agrodolce sauce over the roasted squash on the platter, top with chopped hazelnuts and serve.
Expert tips
- Roast your own hazelnuts if you have time: If you can find raw hazelnuts, roast them at 350°F for 8-10 minutes, then chop them. Freshly roasted nuts taste so much better, and if you're making this for a holiday or special occasion, it's worth the little bit of extra effort.
- Watch the heat on the sauce: Keep the heat low and reduce slowly. The honey could scorch if the heat is to high, and you don't want to over-reduce it.
- Don't mix 2 different types of squash on the same sheet pan: One may cook faster than the other, so keep them separate for easy removal from the oven when done.
FAQ
The agrodolce sauce can be made 1 day ahead. Store in an airtight container in the refrigerator. Reheat gently in a small covered sauce pan over low heat until warm, don't reduce any further.
You can substitute butternut squash for one of the other squashes, but you will need to peel it. Keep it on a separate sheet pan because the cooking time may vary slightly, delicata and acorn will generally cook faster than butternut.
Swap out the honey 1:1 for agave syrup or maple syrup.
More winter squash recipes
Debra's Details: Quick, easy, classic, and festive!
- Quick prep, less than 10 minutes of slicing and chopping.
- Winter squash roasts on a sheet pan for easy cleanup.
- Agrodolce is a classic Italian recipe with sweet and sour flavors.
- Make the sauce one day ahead.
- Cranberries and red wine vinegar add festive flavor and color, making this a beautiful holiday side dish.
- It's gluten-free, dairy-free, and vegetarian, with easy vegan swaps.
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Recipe
Winter Squash Agrodolce with Cranberries
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Equipment
- microplane grater (optional)
Ingredients
- 4 pounds winter squash (a combination of acorn and delicata)
- 4 tablespoons extra virgin olive oil (divided)
- 2 tablespoons minced shallot
- 1 tablespoon finely chopped sage
- 2 garlic cloves
- ¾ cup red wine vinegar
- ¼ cup honey (or agave, or maple syrup)
- ¼ cup dried cranberries
- ¼ cup chopped hazelnuts (or pecans, or walnuts)
- 1 teaspoon kosher salt
- flaky sea salt (for serving, if desired)
Instructions
- Wash the squash well and dry thoroughly with a kitchen towel. Do not peel it.
- Cut the ends off the delicata squash, stand it on one end, then slice it in half lengthwise and use a spoon to scoop out the seeds. Place each half cut-side down, then slice into half circles that are about ½" thick.
- To cut the acorn squash, lay it on its side and carefully cut off the stem end. Then place it cut-side down, cut in half and scoop the seeds out. Place each half cut-side down and slice it into half circles or slice lengthwise along the ridges.
- Preheat the oven to 425°F. Place the racks in the upper and lower third of the oven. Separate each type of squash on two sheet pans, drizzle each with 1 tablespoon of olive oil, season each with ½ teaspoon of kosher salt, toss to coat.
- Bake for 15 minutes, then remove the sheet pans and flip the squash pieces over. Return to the oven, placing the pan that had been on the top rack on the lower rack and vice versa. Bake for another 5-15 minutes until golden brown and soft, transfer to a serving plate.
- While the squash roasts, make the cranberry agrodolce sauce. Mince the shallot and chop the sage finely, then use a microplane grater to grate the garlic (or mince it finely.)
- Place a medium skillet over medium heat. Add the remaining 2 tablespoons of olive oil and once shimmering, add the shallots and a tiny pinch of kosher salt. Cook, stirring frequently until soft and translucent, 3-5 minutes. Add the garlic and sage and stir constantly for 30 seconds to 1 minute, until fragrant. Add the vinegar, honey, and cranberries and bring to a simmer, reduce heat to low and cook, stirring occasionally, until sauce is reduced by about ⅓ and is thick enough to coat the back of a spoon. It should still be pourable.
- Pour the agrodolce sauce over the roasted squash on the platter, top with chopped hazelnuts and serve.
Notes
- Roast your own hazelnuts if you have time: If you can find raw hazelnuts, roast them at 350°F for 8-10 minutes, then chop them. Freshly roasted nuts taste so much better, and if you're making this for a holiday or special occasion, it's worth the little bit of extra effort.
- Watch the heat on the sauce: Keep the heat low and reduce slowly. The honey could scorch if the heat is to high, and you don't want to over-reduce it.
- How to make it vegan: Substitute agave or maple syrup for the honey in a 1:1 ratio.
- Make ahead: The agrodolce sauce can be made one day ahead and stored in an airtight container in the refrigerator. Reheat in a covered sauce pan on low until just warmed through. Don't reduce it any more.
Nutrition
Nutrition information is automatically calculated as an estimate. Calorie accuracy is not guaranteed.
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