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Autumn Caesar Salad with Delicata Squash Croutons

Autumn Caesar Salad with Delicata Squash Croutons pairs crunchy romaine and kale with a creamy Caesar dressing, then tops everything with golden roasted squash rings. The method includes roasting crisp-edged delicata squash and massaging kale for a tender bite.
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Prep Time 20 minutes
Cook Time 25 minutes
Total Time 45 minutes
Servings: 6 servings
Course: Side Dish
Cuisine: American
Calories: 420
Ingredients Equipment Method Notes

Ingredients
  

Delicata squash
  • 1 delicata squash Halved, seeded, and sliced into 1/2-inch half-moons.
Roasting & seasoning
  • 2 tbsp olive oil
  • 1 tbsp maple syrup
  • 0.25 tsp smoked paprika
  • 0.5 tsp salt
Greens & dressing
  • 1 romaine Chopped (large head).
  • 3 cup lacinato kale Stemmed and chopped.
  • 0.5 cup caesar dressing
Toppings
  • 0.5 cup shaved Parmesan
  • 0.25 cup roasted pepitas
Serving
  • 1 lemon Cut into wedges.

Equipment

  • 1 sheet pan

Method
 

Roast the delicata squash croutons
  1. Preheat the oven to 425F. Toss the delicata squash with olive oil, maple syrup, smoked paprika, and salt until evenly coated.
  2. Roast for 22-25 minutes on a sheet pan, flipping halfway, until golden and crisp at the edges. Transfer to a plate to cool slightly while you prep the greens.
Massage and assemble the salad
  1. Massage the lacinato kale with a tablespoon of Caesar dressing for 1 minute to soften. Keep it massaged and set aside.
  2. Toss the chopped romaine and the softened kale with the remaining Caesar dressing until evenly coated. Add the roasted squash croutons over top.
  3. Finish with shaved Parmesan and roasted pepitas. Serve immediately with lemon wedges on the side.

Notes

For the crispiest squash rings, spread them in a single layer on the sheet pan and avoid overcrowding—use two pans if needed. Refrigerate leftovers in an airtight container up to 3 days; for best texture, store dressing separately if possible. Freezing is not recommended. For a lighter option, use a reduced-fat Caesar dressing (or make a Greek-yogurt Caesar style) while keeping the same salad toppings.