Pre heat the oven to 400ºF.
Add the sliced acorn squash wedges to a mixing bowl along with 2 tbsp olive oil, 1 tsp kosher salt, 1/2 tsp cumin, and cracked black pepper. Toss until well coated.
On a large baking sheet lined with parchment paper, arrange the squash wedges to all lay flat in a single layer. In the now empty mixing bowl from step 2, add 2 cups of red table grapes along with 2 tbsp Olive oil, 1/2 tsp Kosher salt, 2 tbsp White wine vinegar, and a few sprigs of fresh thyme. Toss to combine.
Bake the squash in the oven for 20 minutes. After 20 minutes, add the red grapes, sprinkling them evenly amongst the squash wedges. Add the sheet pan with squash and grapes back to the oven for 25 more minutes, or until the grapes are burst and jammy.
Meanwhile, gently score the duck skin with a sharp knife. Season liberally with salt and pepper. Place the duck breast skin side down in a cold stainless steel pan, then turn the heat to medium-low.
Allow the duck fat to render out and cook on medium for 5-10 minutes. When it’s ready to flip, it should be easy to lift off the pan and the skin should be golden. Flip and continue cooking to your desired internal temperature (about 130ºF for medium).
Allow the cooked duck breast to rest for 5 minutes before slicing. Slice, then serve on top of the roasted squash and roasted grapes. Sprinkle with flakey salt.