Ingredients

• 6 898, honeynut, or delicata squash, halved, seeds removed, sliced into 1"-thick half-moons
• ¼ cup extra-virgin olive oil
• Kosher salt, freshly ground pepper
• 1 cup pecans
• 1 tsp. plus ½ cup extra-virgin olive oil; plus more for drizzling
• Kosher salt
• ½ small shallot, finely chopped
• ¼ cup fresh lemon juice
• 2 Tbsp. fresh orange juice
• 2 Tbsp. Dijon mustard
• 4 tsp. pure maple syrup
• Freshly ground black pepper
• 2 small heads of radicchio, leaves separated, torn if large
• ½ medium Asian pear, thinly sliced
• 1 Tbsp. fresh lemon juice
• 3 oz. Piave cheese or Parmesan, shaved
• ¼ cup parsley leaves
• ½ lemon

Instructions

1. Place racks in middle and lower third of oven and set a rimmed baking sheet on each; preheat oven to 450°F. Toss squash with oil in a large bowl; season with salt and pepper. Remove baking sheets from oven and divide squash between them, arranging in a single layer. Roast, rotating sheets halfway through, until browned and tender, 15–25 minutes. Set squash aside; reduce oven temperature to 350°F.
2. Do Ahead: Squash can be roasted 1 day ahead. Let cool, then transfer to an airtight container. Cover and chill. Bring to room temperature or heat slightly in a microwave before using.
3. Toss pecans with 1 tsp. oil in a small bowl; season with salt. Toast on a rimmed baking sheet, tossing halfway through, until slightly darkened and fragrant, 8–10 minutes. Let cool, then coarsely chop. Set ½ cup pecans aside for serving.
4. Blend shallot, lemon juice, orange juice, mustard, maple syrup, and remaining pecans in a blender until mostly smooth. With motor running, gradually stream in ½ cup oil and blend until emulsified and smooth. Season dressing with salt and pepper.
5. Toss radicchio and half of dressing in a large bowl to coat; season with salt and pepper. Arrange on a platter. Toss reserved squash with remaining dressing in the same bowl to coat; season with salt and pepper. Arrange over radicchio.
6. Toss Asian pear with lemon juice in a small bowl. Top salad with Asian pear, cheese, parsley, and reserved pecans. Squeeze juice from lemon half over and drizzle with oil; season with more salt and pepper.
7. Do Ahead: Vinaigrette can be made 1 day ahead. Cover and chill. Bring to room temperature before using.