Drain ricotta cheese in a colander or fine mesh sieve lined with cheesecloth. Lightly break apart and gently press into the sides. Allow to sit for 1-3 hours. If over 1 hour, place in the refrigerator with a bowl underneath to catch the dripping liquid.
In a medium mixing bowl, fold together the ricotta and mascarpone cheeses. Do not overmix.
Add in the powdered sugar vanilla and fold together until there are no dry spots remaining.
Fold in the mini chocolate chips last. Cover the bowl with plastic wrap and refrigerate until ready to use.
Preheat your oven to 350°F and add cupcake liners into a cupcake tin and set aside.
Add the flour, baking powder, baking soda, cinnamon, and salt into a medium bowl and whisk to combine or use a sifter. Set aside.
In the bowl of a stand mixer fitted with a paddle attachment, add the butter and sugar and cream for 1-2 minutes until light and fluffy.
Add the buttermilk, vegetable oil, eggs and vanilla and mix until just combined.
Add in the dry mixture and mix on low speed until there are no dry spots remaining. Scrape the sides and bottom of the bowl and mix for an additional 30 seconds to make sure the ingredients are fully combined, but try not to overmix.
Fill each cupcake liner halfway with batter and gently tap the pan on the counter to remove any air bubbles.
Bake for 10-13 minutes or until a toothpick inserted in each cupcake comes out clean.
Remove from the oven and place on a wire rack to cool completely.
Cream Cheese Frosting:
While the cupcakes are cooling, prepare the frosting by adding the cream cheese and butter in the bowl of a stand mixer with a paddle attachment and cream for 3-4 minutes or until smooth.
Add in the powdered sugar, one cup at a time, combining after each addition. Add in the vanilla last and mix until just combined.
Add the frosting to a piping bag with a large star attachment (I use a Wilton 1M tip)
Take each cupcake and use a cupcake corer, piping tip or a small knife to remove the center of each cupcake (keep the tops of what you remove).
Fill the center of each cupcake with the cannoli filling. Trim the tops to make remove for the filling and replace the top part of the cupcake.
Pipe a generous swirl of frosting on top of each cupcake. Sprinkle with mini chocolate chips and top with a maraschino cherry.
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*If using salted butter, omit additional salt. *Use a vanilla box cake mix, add cinnamon to dry mixture and prepare according to package instructions.