Preheat oven to 425 F (218 C). To prepare squash, use a sharp knife to carefully cut in half lengthwise (from root to tip), then remove seeds with a spoon or ice scream scooper. Slice squash halves into even wedges and leave the skin on.
Arrange squash on a parchment-lined baking sheet. Sprinkle with oil, salt, and pepper and toss to coat. Spread in an even layer.Roast squash for ~15-20 minutes or until tender and golden brown.
In the meantime, prepare dressing by adding balsamic vinegar to a small saucepan. Bring to a gentle boil. Then allow to simmer until it is reduced by half and looks thick (about 10-15 minutes). Watch carefully near the end as it can go from reduced to burnt quickly. You’ll know it’s done when, swirled, it coats the sides of the pan.
At this time, prepare the nut cheese (link to recipe above), or if using store-bought, skip this step.
If toasting pepitas, add to a dry skillet over medium heat and cook, stirring occasionally, until lightly browned - about 3-5 minutes (being careful not to burn).
Next, add sliced shallots to a small bowl with brown rice flour, salt, and pepper and toss to coat. Heat a medium (preferably cast-iron) skillet over medium heat. Once hot, add oil and floured shallots and sauté, stirring occasionally, until lightly golden brown and crispy - ~5 minutes.
To serve, arrange arugula on a platter or serving bowl and top with roasted squash, crispy shallots, dollops of macadamia nut cheese, pepitas, and cranberries or currants. Drizzle with dressing.
Best when fresh, but leftovers can be stored covered in the refrigerator up to 2-3 days (preferably without dressing and squash separate from greens).
*Nutrition information is a rough estimate calculated with all of the dressing and with a combination of avocado and olive oil.