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Step 1
Arrange a rack in the middle of the oven and heat the oven to 400°F. Trim the ends from 1 large delicata squash. Halve lengthwise, scoop out the seeds, then cut crosswise into 3/4-inch thick slices.
Step 2
Place the squash on a rimmed baking sheet. Drizzle with 1 tablespoon of the olive oil, season with 1/2 teaspoon kosher salt and 1/4 teaspoon black pepper, and toss to coat. Arrange into a single layer. Roast, flipping halfway through, until browned and tender, about 30 minutes total. Meanwhile, cook the farro, toast the pumpkin seeds, prepare the dressing, and sear the radicchio.
Step 3
Rinse 1 cup farro. Place in a medium saucepan on medium heat, stirring occasionally, until deepened in color and toasty-smelling, about 5 minutes. Add 3 cups water and bring to boil. Reduce the heat and simmer until cooked through and tender but not mushy, about 20 minutes. Drain and rinse under cool water to stop the cooking. Set aside to drain.
Step 4
Place 1/4 teaspoon of the kosher salt, 1/8 teaspoon of the black pepper, 1/2 teaspoon ground coriander, 1/2 teaspoon ground cinnamon, 1/4 teaspoon ground cardamom, 1/4 teaspoon ground cumin, 1/4 teaspoon ground ginger, 1/4 teaspoon ground turmeric, and 1/8 teaspoon red pepper flakes in a large skillet and stir to combine. Add 1 tablespoon of the olive oil and 1/2 cup pumpkin seeds.
Step 5
Cook over medium heat, stirring occasionally, until the spices deepen in color and the pumpkin seeds are toasted and popping, about 5 minutes. Transfer to a small bowl. Wipe out the skillet with a paper towel and set aside to use later.
Step 6
Finely grate the zest of 1 large lemon into a large bowl (about 1 tablespoon). Juice the lemon until you have 1 tablespoon juice and add to the bowl. Add 3 tablespoons white wine vinegar, 1 tablespoon of the olive oil, and 1 tablespoon honey and whisk to combine. Taste and season with salt and pepper as needed.
Step 7
Cut 1 head radicchio through the core into 8 wedges. Heat the remaining 2 tablespoons olive oil in the reserved skillet over high heat until shimmering. Add the radicchio wedges cut-side down and sear until deep golden brown, about 2 minutes. Flip the wedges to another cut side and sear until browned, about 2 minutes more. Season with a pinch of kosher salt. Remove from the heat.
Step 8
Core and cut 1 medium apple into 1/4-inch thick slices. Finely chop 3 tablespoons fresh parsley leaves. Finely chop chives until you have 2 tablespoons. Crumble 2 ounces blue cheese or fresh goat cheese (about 1/2 cup).
Step 9
Add the farro, squash, radicchio, apple, half the cheese, half the spiced pumpkin seeds, and half the parsley and chives to the bowl of dressing. Gently toss to combine. Transfer to serving plates and garnish with the remaining cheese, pumpkin seeds, and herbs.