Preheat oven to 350°F (175°C). Line a small baking sheet with parchment paper.

Make the crumble: Whisk flour, brown sugar, cinnamon, and salt. Cut in the cold butter until coarse crumbs form. Spread on the baking sheet and bake for 10-12 minutes until golden. Let cool and break apart.

Make the peach topping: In a saucepan over medium heat, melt 2 tablespoons butter. Add peaches, brown sugar, cinnamon, and nutmeg. Simmer 5-7 minutes.

Whisk cornstarch and cold water to make a slurry. Pour into the simmering peaches and cook for 2 more minutes until thickened. Remove from heat and cool completely.

Make the cheesecake filling: In a chilled bowl, beat heavy whipping cream until stiff peaks form. Set aside.

In a separate bowl, beat softened cream cheese until smooth. Add powdered sugar, vanilla, and lemon juice. Beat until well combined.

Gently fold the whipped cream into the cream cheese mixture until smooth. Transfer to a piping bag.

Assemble the cones: Pipe cheesecake filling into waffle cones until 3/4 full. Spoon cooled peach topping over the filling.

Top with cobbler crumble pieces, a dollop of whipped cream, and a maraschino cherry. Serve immediately or chill briefly.