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November 20 2013 by Kristin at The Kitchen Sink in Recipe,Side » 4 comments

Roasted Delicata Squash & Cranberries with Cashews & Arugula

For Thanksgiving this year, we’re headed to Chicago to spend the long weekend with Kevin’s family.  We alternate years between celebrating Thanksgiving with my family and his.  On my family’s years, tradition is king.  We head to Minnesota, where my parents’ dining table is set with the holiday china, and the kitchen counter-turned-buffet is laden with, for the most part, the same dishes year after year, perfected over time.  I know that I can pitch in with chopping the celery or the onions for the stuffing, and that my grandma will peel the apples for the same.  And I know that my mom will handle the gravy.

Roasted Delicata Squash & Cranberries with Cashews & Arugula

I know that a thud of sharp knife meeting a rutabaga will punctuate the morning at some point.  I know that my sister will sleep through much of the cooking.  I know that my step-dad will man the turkey on the charcoal Weber on the back deck, and that my grandfather will slice the bird with the old electric knife.  I know that I will help myself to an immodest amount of mashed potatoes, and I know that I’ll make the pies.  I know that we’ll pose for a family photo on the front steps, shivering from the late November chill in the air.

Roasted Delicata Squash & Cranberries with Cashews & ArugulaRoasted Delicata Squash & Cranberries with Cashews & Arugula

The years we’re with Kevin’s family are much less predictable.  We spent one year at Kevin’s grandmother’s house in Michigan, and we spent two glorious years at our apartment in Chicago.  I would’ve loved to host again this year, but with Kevin’s family stretched out across the country, from Seattle to Boston, it makes more sense for all of us to meet in Chicago, the real beating heart of the family anyway.  We’ll be at his parents’ house there, and we’ve all decided to pitch in on the meal.

Roasted Delicata Squash & Cranberries with Cashews & Arugula

I miss the menu planning and grocery shopping and table setting, and all the other hoopla of hosting, but I’m really looking forward to time with family and to building a new tradition.  I’ve signed myself up to make mashed potatoes and stuffing and pies, but I may just have to sneak in this roasted delicata squash—adorned with toasted cashews and roasted cranberries—too.  It’s a new Thanksgiving side, and this year, I think something new might be just the ticket.
More Thanksgiving inspiration here.

Roasted Delicata Squash & Cranberries with Cashews & Arugula

Roasting cranberries was new to me, and I loved the result.  The cranberries remain tart, but also go a little a jammy.  And they slump pleasantly, without completely losing their shape.  Their tart pop was perfect against the sweet squash.  Leftovers were delicious folded into some quinoa.  If you were looking for a more hefty side, I think farro would work well in this recipe, too.

Serves 4-6

2 medium delicata squash
2 tablespoons olive oil, divided, plus more for drizzling
kosher salt, to taste
several sprigs rosemary
2 cups fresh cranberries
3 tablespoons brown sugar
1/2 teaspoon red pepper flakes
1/2 cup roasted, salted cashews
2-3 cups arugula (optional)

Preheat oven to 400 degrees, with two racks placed in the middle of the oven.  Line two baking sheets with parchment paper and set aside.

Prepare squash (which should be washed).  Trim the ends off the squash, and slice them in half lengthwise.  Using a spoon (a grapefruit spoon works very well), scrape out and discard the seeds.  Slice each half into 1/4-inch thick half moons.  On one of the baking sheets, toss the squash with 1 tablespoon of olive oil and a couple of good pinches of salt.  Spread the squash out evenly, so the slices are flat against the parchment.  Scatter the rosemary sprigs on top of the squash.

Prepare the cranberries (which should also be rinsed).  On the other prepared baking sheet, toss the cranberries with the remaining 1 tablespoon of olive oil, a pinch of salt, brown sugar, and pepper flakes.  Spread evenly.

Roast both the squash and cranberries for 20 minutes.  Remove the cranberries from the oven, increase the heat to 450, and roast the squash for 10-15 minutes longer, until the squash is browned in spots.  For the final few minutes of roasting, arrange the cashews on a small baking tray, and warm them in the oven.

Discard the rosemary sprigs.  Combine the squash and cranberries and serve over a bed of arugula (if desired), topped with the warmed cashews.  Drizzle with additional olive oil, if desired.



4 comments so far. »
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  1. Lora says on November 20 2013 at 3:41 pm:

    Yes please! Can’t wait to see you guys and eat for 4 days straight!

  2. Emily says on November 20 2013 at 9:31 pm:

    This looks delicious. Have so much fun in Chicago — I’m jealous!

  3. Ali says on November 22 2013 at 8:34 am:

    “Sleep through much of the cooking”?!? What about my bartending duties…. one of the most important roles & responsibilities! Have fun in Chicago goes without saying… We’ll MISS you guys. XO

  4. Diane erdahl says on November 29 2013 at 8:07 am:

    Hope the meal was great and the weekend full of fun and love. Missed you too!

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