Caramelized Butternut Squash & Apple with Shallot Vinaigrette

1. Prepare the Vinaigrette

In a small bowl, combine the red wine vinegar, sugar, and 1/8 teaspoon of table salt, stirring until the sugar dissolves. Add the minced shallot, chopped parsley, 2 tablespoons of olive oil, and red pepper flakes. Stir well and set aside to let the flavors meld together.

2. Prepare the Oven and Squash

Adjust your oven rack to the middle position and preheat the oven to 450 degrees Fahrenheit. While the oven is heating, trim the ends off the butternut squash, peel it, then halve it lengthwise and scrape out the seeds. Slice the squash crosswise into 1-inch thick pieces.

3. Roast the Squash

In a large bowl, toss the sliced butternut squash with 2 tablespoons of olive oil and 1 teaspoon of table salt. Spread the squash out on a rimmed baking sheet in a single layer, ensuring the pieces are cut side down. Roast in the preheated oven for 14 to 16 minutes, until the bottoms are beautifully caramelized.

4. Prepare and Add the Apple

While the squash is roasting, toss the apple wedges with the remaining 1 tablespoon of olive oil in the same bowl used for the squash. Once the squash has roasted, place the apple wedges between the pieces of squash on the baking sheet, cut side down. Do not flip the squash. Return the baking sheet to the oven and roast for an additional 8 minutes, allowing the apples to soften and caramelize slightly.

5. Combine and Serve

Using a spatula, carefully transfer the roasted squash and apple to a shallow platter, spreading them out in an even layer. Drizzle the prepared shallot vinaigrette over the warm vegetables, ensuring they are well-coated. Serve this dish warm or at room temperature.