In a medium chilled bowl pour heavy whipping cream and 2 tablespoons vanilla extract. Use a hand mixer on high for 3-5 mins and mix to make whipped cream (look for soft peeks).
Add ½ cup pumpkin puree to whipped cream and mix.
Get a long rectangular platter and take one cookie and spread the whipped cream on it and place on platter. Take another cookie and add whip cream and continue with the cookies and whipped cream to make small stacks on the platter.
You will then turn them on their side and connect the cookies with the whipped cream to make two logs side by side.
Use remaining whipped cream to cover the logs all over to cover them and not see the cookies.
Sprinkle the logs with cinnamon.
Place two toothpicks in each log and cover with saran wrap so that the saran wrap does not touch the logs.
Place in fridge for 3-6 hours depending on time you have. Keep chilled until ready to serve.
Slice on a diagonal for a pretty display!