Preheat oven to 375ºF. Grease a large rimmed baking sheet with oil or line with silicone mat.

Combine oil-vinegar mixture: In a small bowl, combine olive oil, balsamic vinegar, maple syrup, and salt. Set aside.

Prepare squash & brussels sprouts: Prepare squash by peeling, scooping out seeds,  and cutting into one inch cubes. Place on baking sheet. Prepare Brussels sprouts by trimming ends and cutting in half lengthwise. Add to baking sheet with the squash, pour on the vinegar-oil mixture, and stir with spatula to combine.

Roast vegetables for 20 minutes, then stir and roast for another 10-15 minutes, until squash is soft and brussels sprouts are golden.

Make the dressing: combine all ingredients into small blender on high speed until smooth or combine in medium bowl and whisk vigorously by hand.

Toss and serve: When the vegetables have finished roasting, transfer to casserole or serving dish. Add dried cranberries, sliced almonds (reserving some for garnish on top if desired), and dressing. Gently stir to combine. Best enjoyed warm.