Roasted Squash with Crispy Bread and Almond Aioli


If I had to choose one squash and only one squash to eat for the rest of my life it’d be Delicata ferrrr sure. To me it is the sweetest, most full flavored and meaty of the winter squashes save for Kabocha which unfortunately more often turns chalky as it roasts. You can honestly use any squash you’d like here, or even halved sweet potatoes, so do you! Just my two cents….

Active Time: 20 Mins

Total Time: 50 mins

Roasted Squash with Crispy Bread and Almond Aioli


  • 2 pounds delicata squash (about 2 medium)
  • 10 garlic cloves
  • 5 big thyme sprigs
  • 1 cup tender herbs (parsley, dill, cilantro and/or chives)


  • 1 cup olive oil
  • 6 ounces sourdough bread
  • ¾ cup slivered, blanched almonds
  • 3 tablespoons sherry vinegar, plus more
  • Kosher salt, freshly ground black pepper

1. Roast the squash:

  • Arrange a rack in the bottom of your oven. Preheat the oven to 450.
  • Cut 2 pounds delicata squash in half lengthwise. Scoop out an discard the seeds. Cut crosswise into 1” inch half moons. Transfer to a rimmed baking sheet.
  • Smash 8 garlic cloves, but leave them in their skins. Add to the baking sheet with 5 big sprigs of thyme. Drizzle with 2 tablespoons olive oil; season with salt and pepper.
  • Roast, until deeply caramelized underneath, 20-25 minutes.
  • While the squash roasts, tear 6 ounces sourdough into big craggy 2” ish pieces. Transfer to a bowl and drizzle with 2 tablespoons olive oil. Season the bread with salt and pepper.
  • After 25 minutes, add the torn bread to the sheet along with the squash. Return to the oven to roast until bread is golden brown and crisp 10-15 minutes longer.

2. Make the almond aioli:

  • In a blender, combine ¾ cup blanched, slivered almonds, and 2 garlic cloves. Blend until pulverized.
  • Add ¾ cup olive oil, ¼ cup water, 3 tablespoons sherry vinegar, and 2 teaspoons salt. Blend on high 1 minute. If it’s still quite thick, continue adding water a few tablespoons at at time until creamy and similar in consistency to mayonnaise. (You may end up needing quite a bit more water). Taste and add more salt as needed!

3. Serve:

  • In a small bowl, drizzle 1 cup coarsely chopped mixed tender herbs lightly with sherry vinegar. Season with salt.
  • Swoosh some almond aioli onto a serving platter (you may have more than you need--save the rest!).
  • Top with roasted squash, fried bread, and the dressed herbs.

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