Mix butternut squash with squash seed oil. Sprinkle with salt and pepper. Roast on a rimmed baking sheet for 20 min @ 400F until tender.
Mix kale with lemon juice and salt in a bowl. Massage juice and salt into kale for a few minutes and let rest.
Garlic Bread Bites:
Heat squash oil in large skillet over medium heat.
Add crushed garlic and heat until fragrant, about 30 sec.
Add bread cubes and stir until coated with oil and garlic. Season with salt and pepper. Toast in skillet for about 5 minutes, tossing until sides get a little crisp and golden. Careful not to let the oil get too hot and start to smoke. The garlic will get a little crispy and some of the seeds from the bread will break off and get toasted - these bits are excellent sprinkled over the squash salad.
On a platter or in individual bowls, add kale, squash and bread cubes together. Dress with vinaigrette. Sprinkle with salt and pepper to taste.
In a blender or Cuisinart, pureé the pear. Add in thawed cranberries and pulse to break up the cranberries. Add in honey mustard and balsamic vinegar. Drizzle in olive oil together and blend until completely combined. Season with salt and pepper and extra honey if desired.