In a medium bowl, beat cream cheese and sugar using an electric hand mixer until smooth, about 1 minute. Add heavy cream and vanilla and beat until medium peaks form, about 1 minute. Set aside.
In a separate large bowl, beat milk, pumpkin puree, pudding mix and pumpkin pie spice using an electric hand mixer, until combined, about 1 minute.
Spread a thin layer of cream cheese mixture in the bottom of 9x13-inch baking dish. Top with a layer of 6 graham crackers. Spread half the pudding mixture evenly over the graham crackers. Top with half of the cream cheese mixture. Drizzle with half of the caramel. Repeat with remaining pudding mixture and graham crackers, ending with a layer of the cream cheese mixture.
Cover with plastic wrap and refrigerate for at least 4 hours. Drizzle with remaining caramel, and garnish with pecans. Slice and serve.
