Preheat your oven to 425° F.
In a small bowl combine the acorn squash, ⅓ cup olive oil, pomegranate vinegar, honey and salt. Mix well to make sure that all the slices are covered.
Roast on a sheet pan lined with parchment paper for 15 minutes, then flip each slice and continue roasting for another 5 minutes.
Meanwhile in a large skillet over medium high heat, add 2 tablespoons of olive oil, and the cubed bread.
Allow the bread to toast up while shaking the pan every minute or so until the cubes get toasty.
Remove the bread from the pan and set aside.
Using the same skillet, add the remaining 2 tablespoons olive oil, and the minced garlic.
Saute for 1-2 minutes or until the garlic becomes fragrant, and then add in the shaved brussels sprouts.
Stir and saute until the brussels sprouts soften, about 5-6 minutes.
Remove from heat, and cool.
Make the salad dressing- In a small jar or bowl, combine the vinaigrette ingredients and whisk vigorously or shake really well.
Assemble the salad- Lay the brussels sprouts on a platter, with the acorn squash and bread cubes on top. Sprinkle with the pomegranate seeds and drizzle with the dressing.