Make the streusel: Preheat oven to 375°. Bake oats, pumpkin seeds, and walnuts on a rimmed baking sheet until light golden, about 10 minutes; let cool. Transfer to a food processor. Add the remaining 6 ingredients and pulse until crumble forms. Spread on rimmed baking sheet; bake until golden and crispy, occasionally breaking up lumps, 18-20 minutes. Let cool.
Make the compote: Bring first 7 ingredients and 1 1/2 cups water to a simmer in a large saucepan over medium heat. Cover and simmer until pumpkin is just tender, about 7 minutes. Add pears and vanilla; cook uncovered, stirring often, until pears are tender, about 10 minutes. Using a slotted spoon, transfer pumpkin-and-fruit mixture to a medium bowl. Simmer syrup in pan until reduced to 1/2 cup, 3-5 minutes
Assemble the crisps: Arrange ramekins on a rimmed baking sheet. Divide compote among ramekins. Drizzle each with 1 Tbsp. reserved syrup. Bake until filling is bubbling at edges, 25-30 minutes. Top with streusel and serve.