1⁄2 cup chestnuts, roasted, peeled, and coarsely chopped
11 sage leaves, divided
Preheat the oven to 350ºF. In a pot filled with cold water, add the farro, lightly season with salt, and bring to a simmer. Cook 20 to 30 minutes or until tender.
Drain cooked farro and toss with 1⁄4 cup olive oil. Spread farro on a baking tray and let cool completely. Cut the squash in half, and scoop out the seeds. If necessary for each squash half to sit upright, cut off a small section of the base.
Season squash with 2 tablespoons of olive oil, salt, black pepper, and a few grates of nutmeg. Heat a cast-iron pan over medium-high heat and brown the cut edges of the squash, working in batches if necessary.
Transfer the cast-iron pan to the oven after adding a leaf of sage to each section of squash, and cook until just tender, but not collapsing. Remove the squash from the oven and let cool slightly. In a small sauté pan, warm the farro with the remaining 2 tablespoons of olive oil.
Add the cherries, chestnuts, and 3 chopped leaves of sage and stir to combine. Fill the squash cavities with the farro mixture and serve.