Preheat oven to 425* and prepare a baking sheet with parchment.
With a sharp knife, carefully cut the acorn squash in half from root to tip. Remove the seeds with a spoon, and slice squash into ½” thick pieces.
Arrange squash in a single layer on the parchment. Sprinkle with oil, salt, pepper and toss to coat.
Bake for 40 minutes, flipping half-way through until golden with some dark spots here and there.
Line a plate with two layers of paper towels and set aside.
In a large saucepan heat the vegetable oil over medium-high heat until it starts to shimmer.
Slowly add the shallot slices in batches, transferring to the paper towel lined plate with a slotted spoon once they crisp up and turn gold.
In a medium sized bowl whisk together the tahini, maple syrup, lemon juice and salt. Once combined, slowly whisk in a bit of water at a time until the consistency is slightly runny.
Grab your favorite platter or large bowl and fill it with lettuce. Layer on pieces of squash, sprinkle with pepitas and finally the crispy shallots. Drizzle with dressing and serve with extra crispy shallots for more crunch!