For the vinaigrette
1. Combine all ingredients in a small bowl or Mason jar with lid and whisk or shake to combine.
For the salad
1. Preheat oven to 450°. Cut squash into 1-inch cubes and place in large bowl. Toss with just enough olive oil to coat and season with salt and pepper. Place squash in single layer on a parchment-lined baking sheet and roast until golden brown and tender.
2. While squash cools, combine arugula and cherries in a large bowl and toss with enough vinaigrette to lightly coat leaves. Gently fold in squash and toss with your hands to combine.
This salad is best plated individually. Place a handful of greens and squash on each of four plates, and garnish with chevre and pepitas.