Whole Grain Pasta with Grilled Chicken and Butternut Squash

Preheat the oven to 450 degrees F (230 degrees C).

Combine squash, 2 tablespoons olive oil, rosemary, sage, thyme, oregano, basil, sea salt, and pepper in a large bowl; toss until squash is coated with herbs. Transfer to a sheet pan.

Place in the preheated oven and cook until squash pieces turn golden brown on the bottom, 15 to 20 minutes. Remove from oven, flip with spatula, and cook until tender, 15 to 20 more minutes.

While squash is cooking, preheat an outdoor grill for medium-high heat and lightly oil the grate.

Brush chicken with remaining 1 tablespoon olive oil and season with sea salt and pepper.

Cook chicken on the preheated grill until no longer pink in the center and the juices run clear, 3 to 4 minutes per side. An instant-read thermometer inserted into the center should read at least 165 degrees F (74 degrees C). Remove to a plate and cut into thin slices.

While chicken is cooking, bring a large pot of lightly salted water to a boil. Add penne and cook, stirring occasionally, until tender yet firm to the bite, about 11 minutes. Drain pasta and transfer to a large bowl. Top with roasted butternut squash and all oil and herbs from the sheet pan. Add chicken slices and sprinkle with Parmigiano-Reggiano cheese. Drizzle with remaining 2 tablespoons olive oil if pasta seems dry.