Preheat oven to 425°F.
Whisk together 3 tbsp. Extra Virgin Olive Oil, honey, 1 ½ tbsp. fresh thyme leaves, and a good pinch of salt. Toss acorn squash slices in the mixture and arrange in a single layer on a large baking sheet. Roast for 20 minutes.
Remove baking sheet from oven and add the halved figs. Toss to coat with the EVOO mixture. Return to the oven for an additional 10-15 minutes, or until the figs have caramelized. (If using dried figs, cook for 5 minutes only. This will soften them)
Make the dressing: Whisk together the remaining EVOO, Black Mission Fig Dark Balsamic, lemon juice, remaining ½ tbsp. thyme, orange zest, salt & pepper to taste.
Place the arugula in a large bowl. Arrange the roasted squash, figs, feta crumbles, and pomegranate seeds on top. Drizzle with salad dressing. Enjoy!