In a blender, combine about 2 cups of vanilla ice cream, 1 cup of milk, 1 cup of pumpkin puree, and 1 teaspoon of pumpkin pie spice. Blend at high speed for 30-45 seconds until creamy and smooth.

While the milkshake is blending, take your serving glasses and sprinkle about a tablespoon of crushed graham crackers into the bottom of each glass.

Once your milkshake is perfectly blended, carefully pour it into each prepared glass, filling them about three-quarters full.

Top each glass generously with whipped cream and sprinkle extra crushed graham crackers and a dash of pumpkin pie spice.

Insert a straw into each glass and serve immediately for the best texture and flavor.