First, make the cupcakes. Preheat oven to 350F and line two muffin pans with 20 muffin liners.
In a small bowl, whisk together the ground flaxseed with the water and set aside to thicken.
In the bowl of a stand mixer, combine the sugar, flour, baking powder, baking soda, and salt.
Add in the vegan butter, and beat on low until it's incorporated and has a sandy texture.
In a small bowl, whisk together the oil, flaxseed mixture, nondairy yogurt, cherry & vanilla extracts, nondairy milk, and maraschino cherry juice. Add them to the dry ingredients. Beat on medium-low until everything is just combined. Add in food coloring until you reach your desired color, and mix until well incorporated.
Divide batter evenly among the prepared cupcake liners. Bake cupcakes for 20-25 min until they are fluffy and a toothpick inserted in the center comes out clean.
While the cupcakes cool, prepare the frosting.
In the bowl of a stand mixer, beat the shortening and vegan butter together until completely smooth and creamy. Add in the powdered sugar, 1 cup at a time, until a thick frosting forms. Add in the salt and vanilla extract. You can add a few spoonfuls of nondairy milk if it's too thick.
When the cupcakes are cooled completely, carve out the center of each cupcake using a small spoon (I used a 1 teaspoon measuring spoon). Spoon 1 teaspoon of cherry pie filling in the cavity, and replace the carved out piece of cupcake to cover the filling. Repeat with all.
To finish, decorate them with the frosting. I used a 1M tip. To make the "blood" on top, I simply mixed some of the liquid from the cherry pie filling with a little water to make it more runny, and drizzled it on top. Add on plastic vampire teeth if desired!