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Autumn Caesar Salad with Delicata Squash Croutons

Autumn caesar salad with delicata squash croutons features crisp romaine and kale tossed in creamy Caesar dressing, topped with golden roasted squash rings. Roasting at high heat creates crunchy, edge-caramelized croutons that pair with shaved Parmesan and pepitas.
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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.
olive oil
  • 2 tbsp olive oil
maple syrup
  • 1 tbsp maple syrup
smoked paprika
  • 0.25 tsp smoked paprika
salt
  • 0.5 tsp salt
romaine lettuce
  • 1 large head romaine Chopped.
lacinato kale
  • 3 cup lacinato kale Stemmed and chopped.
caesar dressing
  • 0.5 cup Caesar dressing
shaved Parmesan
  • 0.5 cup shaved Parmesan
roasted pepitas
  • 0.25 cup roasted pepitas
lemon
  • 1 lemon Cut into wedges.

Equipment

  • 1 sheet pan

Method
 

Roast the delicata squash croutons
  1. Preheat oven to 425F. Toss delicata squash with olive oil, maple syrup, smoked paprika, and salt until evenly coated, with the squash spread out in a single layer for even browning.
  2. Roast 22-25 minutes, flipping halfway, until golden and crisp at the edges, then set aside to cool slightly so the rings stay crunchy.
Massage kale and assemble salad
  1. Massage the lacinato kale with 1 tablespoon of Caesar dressing for 1 minute to soften, until it looks slightly darker and more tender.
  2. Toss the romaine and kale with the remaining Caesar dressing until well coated and glossy, with no dry patches of greens.
  3. Top the salad with the roasted delicata squash croutons, shaved Parmesan, and roasted pepitas so the crunchy pieces sit on top rather than sinking in.
  4. Serve immediately with lemon wedges on the side so each bite can be finished with fresh juice.

Notes

For the crispiest squash rings, make sure the sheet pan is single-layer and avoid overcrowding; you can cool the roasted squash 5-10 minutes before topping. Store salad components separately in the fridge: roasted squash and dressing-tossed greens keep 3 days, but assemble right before serving for crunch. Freezing is not recommended. For a lighter option, use a reduced-fat Caesar dressing and shave Parmesan more lightly to cut calories without changing the roasted crouton method.