1. Preheat oven to 450 degrees Fahrenheit (230 degrees Celsius). Line two baking sheets with Gefen Parchment Paper.
2. Peel and rinse all vegetables and pineapple. Slice carrots, sweet potato, and yellow squash (if using) on an angle, into 1/3-inch (one centimeter) slices, and then cut into half-moons. Cut onion and beets in half and then slice, cut side down, into thin wedges. Cut the top off the garlic head, if using, so the cloves are exposed.
3. Cut pineapple into quarters lengthwise, and remove hard core. Slice into 1/3-inch-thick (one-centimeter) slices, then cut each piece in half.
4. Place vegetables and pineapple pieces onto baking sheets in individual sections, and drizzle with oil. Roast for 30 minutes. Meanwhile, combine dressing ingredients.
5. Flip vegetables and pineapple and brush with dressing. Roast an additional 30 minutes, checking for doneness after 20 minutes.
6. Remove from oven and combine vegetables in a pan. Pour dressing over vegetables and toss gently to coat. Serve hot or cold.