Using a stand mixer with whisk attachment pour cream into bowl and start mixer on low speed. Add sugar and vanilla extract while mixing on low. Once cream starts to thicken, increase mixer speed. Continue mixing until you have reached a stiff peak.
Transfer cream into a pastry bag with a 5 star tip. Pipe cream into bowl of spoon.
Garnish cream with Hershey’s Dark Chocolate Syrup and Maraschino Cherries.