Roasted Acorn Squash With Caramelized Red Onions and Honey-Date Vinaigrette

Pair wedges of roasted acorn squash with thick slices of jammy, caramelized red onions, then top it with an orange juice- and honey-tinged vinaigrette for a delicious side. The key to its success is our unique roasting technique.

Roasted Acorn Squash With Caramelized Red Onions and Honey-Date Vinaigrette
Servings 4
Difficulty Medium

Ingredients

Instructions

  1. 1

    Adjust oven racks to middle and lowest positions. Place a large rimmed baking sheet on the lowest oven rack. Preheat oven with baking sheet to 475°F (245℃). Line a second large rimmed baking sheet with aluminum foil. Cut each onion half through the root end into 4 (about 1 1/2–inch-thick) wedges. Brush onion wedges all over with 1 tablespoon oil. Arrange wedges, cut side down and evenly spaced, along outer edges of prepared foil-lined baking sheet. Cover baking sheet tightly with aluminum foil. Roast on middle rack for 10 minutes.

  2. 2

    While onions are roasting, cut each squash half crosswise into four 1 1/2– to 2-inch-thick half-moon wedges; transfer to a large plate. Using a pastry brush, brush squash wedges with 2 tablespoons oil, and sprinkle evenly with 1 teaspoon salt, and 1/2 teaspoon pepper.

  3. 3

    After onions have roasted for 10 minutes, carefully remove the empty preheated baking sheet from oven. Working quickly, arrange squash wedges on the preheated baking sheet, cut side down and evenly spaced, along outer edges of baking sheet (spoon the squash pieces into each other to maximize space). Roast on lowest oven rack. Let onions and squash roast until onions are softened and translucent, 10 minutes longer.

  4. 4

    Remove onions from oven and carefully remove foil. Brush with 2 tablespoons oil and sprinkle with 1 teaspoon of the salt and remaining 1/4 teaspoon pepper. Return to middle oven rack and continue to roast both onions and squash, uncovered and flipping squash once halfway through, until bottom sides of onion wedges are lightly browned and squash are browned, about 20 additional minutes.

  5. 5

    While vegetables roast, place dates, orange juice, vinegar, honey, pinch of chile powder, and remaining 3 tablespoons oil, and 1/2 teaspoon salt in a small bowl. Stir and mash dates using the back of a spoon until mixture is thickened and creamy but still loose enough to drizzle.

  6. 6

    Transfer roasted squash and onion wedges to a large serving platter. Drizzle with date-orange dressing and garnish with pistachios. Serve.

  7. 7

    Pastry brush, 2 rimmed baking sheets

  8. 8

    You can use hot honey in place of the regular honey. If using hot honey, omit the pinch of chile powder.

  9. 9

    The dressing can be made ahead and refrigerated for up to 3 days. Bring to room temperature and whisk to recombine,thinning with a teaspoon of water if necessary.

Chef's Tips

  • Leftover roasted vegetables and be refrigerated in an airtight container for up to 5 days. Serve at room temperature or reheat in oven.