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Roasted Butternut Squash with Sage & Bourbon Cranberries — The Side Dish That Holds the Table Together

Early November. The Thanksgiving planning is underway and this year the gathering is the largest yet: twenty-five people confirmed, including three cooking-class regulars who have graduated from students to friends to Thanksgiving guests. The graduation from stranger to student to friend to dinner guest is the trajectory of the cooking class community, and the community is the reward, and the reward is the kitchen full of people who came because the food brought them and the food is Fumiko's and the people are mine and the convergence is the life.

I made a practice batch of the miso-butter turkey — the rehearsal, the dry run, the professional approach to a holiday meal. The turkey was perfect. The perfection is earned: this is the sixth year of the miso-butter turkey, the sixth Thanksgiving of the recipe that has become my signature, the recipe that people request, the recipe that is in the book. The book is the recipe's biography. The recipe is the book's soul.

I have been feeling good — specifically, unusually good. The anxiety has been quiet for months. The medication is working. The yoga is working. The writing is working. The combination of all four pillars (medication, yoga, writing, cooking) has produced a stability that feels, for the first time in twenty-four years, like the natural state rather than the managed state. The stability feels like: maybe I don't need the medication anymore. Maybe the other three pillars are enough. Maybe the pill is a crutch and the mat and the pen and the stove are the legs. The thought is seductive. The thought is dangerous. The thought is the thought that will lead to the decision that will lead to the panic attack at Trader Joe's, but I do not know that yet. I know only: I feel good. I have not felt this good in years. The good feels permanent. The permanent is the illusion. But I do not know that yet.

With twenty-five people confirmed and the miso-butter turkey already rehearsed to perfection, my attention turned to what would surround it — the sides that frame the centerpiece without competing with it. This roasted butternut squash with sage and bourbon cranberries has become exactly that: warm, a little bold, just sweet enough to balance the umami of the turkey, and beautiful on a table full of people who came because the food brought them.

Roasted Butternut Squash with Sage & Bourbon Cranberries

Prep Time: 20 minutes | Cook Time: 40 minutes | Total Time: 1 hour | Servings: 8

Ingredients

  • 1 large butternut squash (about 3 lbs), peeled, seeded, and cut into 1-inch cubes
  • 3 tablespoons olive oil, divided
  • 1 teaspoon kosher salt, plus more to taste
  • 1/2 teaspoon black pepper
  • 1/2 teaspoon smoked paprika
  • 12 fresh sage leaves
  • 1 1/2 cups fresh or frozen cranberries
  • 3 tablespoons bourbon
  • 2 tablespoons maple syrup
  • 1 tablespoon unsalted butter
  • 1/4 teaspoon cinnamon
  • 1/4 cup toasted pecans, roughly chopped (optional, for serving)

Instructions

  1. Preheat and prep. Preheat your oven to 425°F. Line a large rimmed baking sheet with parchment paper.
  2. Season the squash. Toss the butternut squash cubes with 2 tablespoons of the olive oil, salt, pepper, and smoked paprika until evenly coated. Spread in a single layer on the prepared baking sheet, making sure pieces aren’t crowded.
  3. Roast. Roast for 35–40 minutes, flipping once halfway through, until the squash is tender and caramelized on the edges.
  4. Fry the sage. While the squash roasts, heat the remaining 1 tablespoon olive oil in a small skillet over medium-high heat. Add the sage leaves in a single layer and fry for 30–45 seconds per side until crisp and fragrant. Transfer to a paper towel-lined plate and sprinkle lightly with salt.
  5. Make the bourbon cranberries. In the same skillet over medium heat, melt the butter. Add the cranberries, bourbon, maple syrup, and cinnamon. Cook, stirring occasionally, for 6–8 minutes until the cranberries burst and the sauce thickens slightly. Season with a pinch of salt.
  6. Assemble and serve. Transfer the roasted squash to a serving platter. Spoon the warm bourbon cranberries over the top, then scatter the fried sage leaves and toasted pecans over everything. Serve immediately.

Nutrition (per serving)

Calories: 185 | Protein: 2g | Fat: 9g | Carbs: 24g | Fiber: 4g | Sodium: 230mg

Jen Nakamura
About the cook who shared this
Jen Nakamura
Week 419 of Jen’s 30-year story · Portland, Oregon
Jen is a forty-year-old yoga instructor and divorced mom in Portland who traded panic attacks for plants and never looked back. She's Japanese-American on her father's side — third-generation, with a family history that includes wartime internment and generational silence — and white on her mother's. Her cooking is plant-forward, intuitive, and deeply influenced by both her Japanese grandmother's techniques and the Pacific Northwest farmers market she visits every Saturday rain or shine. Which in Portland means mostly rain.

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