In a large bowl, whisk together the pumpkin puree, maple syrup, brown sugar, vanilla, pumpkin pie spice, ½ teaspoon cinnamon, and ½ teaspoon salt until completely smooth.
Using a hand mixer, beat the dairy-free whipping cream until it holds soft peaks. Gently fold about half of the whipped cream into the pumpkin mixture. Fold in the remaining whipped cream until smooth and fluffy. Do not overmix.
Preheat the oven to 350°F. Line a small baking sheet with parchment paper. Toss the crushed Homefree cookies with the maple syrup, melted dairy-free butter or oil, ½ teaspoon cinnamon, and a pinch of salt. Spread in an even layer on the baking sheet.
Bake for 8–10 minutes, stirring once halfway through, until the cookie crumbs are fragrant and lightly crisp. Let cool completely. The crumbs will become crunchier as they cool.
Spoon about 2 tablespoons of cookie crunch into the bottom of each of six small parfait glasses or coupe glasses. Top with about ½ cup pumpkin filling. Add another layer of cookie crunch, followed by another layer of pumpkin filling.
Top each parfait with a small dollop of dairy-free whipped cream, if desired. Finish with a Homefree Mini Cookie and a light sprinkle of pumpkin pie spice.
Refrigerate for at least 1 hour before serving. For the best texture, add the final cookie garnish just before serving.