Slice off small portions of top and bottom of the squash so that it sits flat on a cutting board. Cut the squash in half and scoop out the seeds (save them to roast). Cut each half into slices about 1/3" thick and place in a single layer on a large baking sheet.
Drizzle the prepared squash with half the olive oil, half the maple syrup, salt and pepper.
Roast for 20 minutes.
Remove the baking sheet from the oven, gently flip each piece of squash and drizzle the other side with the remaining olive oil, maple syrup, salt and pepper.
Return to the oven and roast for an additional 20 minutes until squash is crispy and golden brown on the edges while the flesh is tender and starting to caramelize.