Preheat oven to 425°F degrees.
Prepare delicata squash by cutting off the ends of each. Cut each piece in half lengthwise. Scoop out the seeds, then slice into 1/4 to 1/2" pieces.
Pour olive oil, maple syrup, and cinnamon into a medium sized bowl. Stir to combine, then add the delicata squash and stir again to coat.
Line a baking sheet with parchment paper, then spread out the delicata squash pieces on the pan. Bake for 15 minutes, then flip each piece and bake for another 10 minutes.
Remove from the oven and let cool about 15 minutes.
While the delicata squash is baking, place a pan on the stove and put on medium heat. Add chopped bacon and cook until brown and crispy, stirring on occasion. Remove pieces with a slotted spoon and place on a paper towel to cool.
Make the dressing by adding all of the ingredients to a jar. Tighten the cover on the jar and shake until it is well combined.
Gather and measure the rest of the ingredients (mixed greens, dried cranberries, and pecans). Thinly slice the apple and the onion.
When the delicata squash and bacon have mostly cooled, put all the ingredients except for the dressing and 1/3 of the squash and apple pieces in a large bowl. The reserved squash and apple will be used for layering over the top of the salad.
Just prior to serving, pour half of the dressing over the salad and stir to combine.
Transfer the salad to a large platter or bowl. Layer the top with the rest of the squash and apple. The rest of the dressing can be served on the side for drizzling over the top.
It's also best to eat the same day as it doesn't save well.