In a mixing bowl, combine Cool Whip with pumpkin purée, pumpkin spice, pudding mix, and vanilla. Mix well until uniform.
Line a plate with parchment paper, and scoop your pumpkin mixture into even size blobs. You can use a cookie scoop to make this even.
Melt chocolate with coconut oil in 30 second increments in the microwave, stirring in between so it doesn’t burn. Drizzle chocolate over your pumpkin ice cream bites, top with crushed graham cracker, and freeze until completely solid, 4 to 6 hours. Enjoy!