Step 1

Preheat the oven to 425°F. Peel the butternut squash until you reach the pure yellow-orange layer (there should be no white remaining). Cut the squash in half lengthwise. Scoop out the seeds/stringy flesh. Place the squash onto a sheet pan and drizzle generously with olive oil. Rub to coat evenly. Season with salt and freshly cracked black pepper. Roast the squash, halved-side down, for 20 minutes.

Step 2

Meanwhile, heat a 2qt saucepan over medium heat. Add about 2 teaspoons of olive oil. Place the sage leaves in the hot oil and fry until crisp, just a minute or so. Transfer the sage to a plate. Add the sliced shallot to the oil. Saute for a few minutes until caramelized. Season with a pinch of salt.

Step 3

Stir in 3 tablespoons of maple syrup, 2 tablespoons of white wine vinegar, the dijon, and water. Bring the mixture to a simmer. Lower the heat and cook for about 5 minutes until syrupy. Transfer the shallots to a mixing bowl. Reserve the maple glaze.

Step 4

Remove the squash from the oven. Use a sharp knife to score the outside of the squash in small increments (see photos above). Cut each slice about ¾” of the way into the squash, without cutting all the way through. Brush the maple glaze over the squash. Continue to roast for about 30 more minutes, or until tender.

Step 5

Add 1 tablespoon of maple syrup and the remaining 1 tablespoon of white wine vinegar to the shallots. Whisk to combine. Slowly whisk in the vegetable oil. Season with a pinch of salt to taste.

Step 6

Heat a skillet over medium heat. Add enough olive oil to coat the bottom. Add the pecans. Toast for a couple of minutes until golden and fragrant. Stir in the remaining 3 tablespoons of maple syrup and a pinch of salt. Simmer for about 3 minutes until reduced.

Step 7

Toss the arugula with half of the shallot vinaigrette and arrange it onto a platter. Use a metal spatula to carefully transfer the butternut squash from the sheet pan to the platter. Top with the maple pecans, goat cheese, and fried sage. Drizzle the remaining vinaigrette over the squash. Sprinkle with flaky sea salt.