Back-to-School Family Dinner - Roasted Chicken & Kabocha Squash

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Eat Flawelessly this School Year

Prep Time: 20 minutes
Cook time 1 hour
Serves: 6

Back-to-School time is not only an overwhelm for my kid but September also sends my husband and I back into a NYC business pace that makes us feel like we are still on the roller coaster from summer vacation! I am committed to cooking for my family and the last thing I have time to do is make two meals (one for kids and one for grown-ups)! This combo of roasted chicken and kabocha squash is my go to for any week night AND everyone loves it (including our Nanny Marissa and the kid that stayed late from his play date)!

STEP 1: Always have chicken and squash on the grocery list.

I usually do a big online shopping order on Sundays for my weekly grocery shopping. It only takes me about 10 minutes because I use the “shop from past orders” function. I basically fill my cart with last week’s stuff and add a few in-season or “store recommendations”.

When I say “Always have chicken on the grocery list”, I don’t mean frozen chicken nuggets. I mean bone-in, skin-on chicken (but yes I have chicken nuggets on there too :). You can buy a whole roaster, whole cut up chicken or parts like breasts or legs. If you cannot find kabocha squash, use butternut but try to get kabocha as it will change your family’s life!


Roasted Chicken Legs


  • 8 bone-in, skin-on whole (with the thigh) chicken legs

  • Avocado oil (or other high-temperature oil)

  • Tablespoon salt

  • Tablespoon ground black pepper


  1. Preheat oven to 400 degrees. Make sure you have your oven racks spread far enough apart that you can accommodate both the chicken and the squash sheet pans. Pro Tip: if you have a “convection” setting on your oven, use it as this moves the air in the oven and will better handle baking the chicken and squash simultaneously.

  2. Line a rimmed cookie sheet with foil

  3. Spread chicken out on foil and coat, on every side, with avocado oil

  4. Place chicken skin-side-up and sprinkle with salt and pepper


Roasted Kabocha Squash


  • 1 Kabocha squash, cut up and seeded

  • Avocado oil (or other high-temperature oil)

  • Teaspoon salt

  • Teaspoon ground black pepper

  • 5 Tablespoons butter and a sprinkle more salt


  1. Line a baking sheet with foil

  2. Cut up and seed your kabocha squash. Of note, this may be the hardest plant to cut on the planet! Make sure your knife is sharp ( I use a freshly sharpened butcher’s knife) and from a good step back, I take my first wack! …think “chopping down a tree”. Then, when my knife is embedded in the first inch of flesh, pick up the squash via the knife handle I am holding and smash it against the cutting board. THEN, I use my body weight to pierce through the rest of the squash. I never get it totally centered and that does not matter. Remove the seeds with a spoon and cut the two sides into two or three parts each.

  3. Spread the kabocha chunks on the lined cookie sheet and coat, on every side, with avocado oil

  4. Sprinkle orange flesh with salt and pepper and then turn the chunks over so that the skin side is facing up.

  5. Bake chicken and squash simultaneously, on different oven racks, for 1 hour.

  6. After roasting, remove chicken and squash from oven.

  7. Plate chicken on serving platter and throw something like herbs on the platter to make it even more beautiful.

  8. Scoop the flesh out of the skins of the squash using a large spoon. Place flesh in mixing bowl (or directly in the serving bowl if you want to save washing another dish!) with the butter at the bottom (this will melt the butter as you go) and discard the skins. I wear my dish washing gloves for this ‘cause boy is it hot! Note, the kabocha squash will look dry and chalky after roasting but have no fear! -butter is on the way!

  9. Mix the melted butter into the squash until it looks like chunky mashed potatoes. Sprinkle with salt.

FINAL STEP: Set the table and throw a green veggie into the mix. Something simple like steamed broccoli, a salad or blanched green beans.

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Wanna add Dessert?

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