Preheat a griddle to 325-350 degrees.( My old griddle gets really hot)
In a large skillet, over medium heat, melt 1/2 cup butter and brown sugar together. Add the pineapple rings and cook until caramelized.
In a large mixing bowl, combine flour, baking powder, baking soda and salt.
In a small bowl, whisk together milk, granulated sugar and vanilla.
Pour the wet ingredients into the dry and mix until just-combined. Add a 1/4 cup melted butter and mix well.
Lightly grease the preheated griddle and wipe away any excess oil. Using a 1/3 cup measuring cup, portion out pancake batter onto the hot griddle. Place a pineapple ring in the center of the batter, press down gently, and add a Maraschino cherry to the center of each ring.
Allow the pancakes to cook until bubbles form along the top of the batter. Flip and cook the other side until pancakes are golden brown and cooked inside.
Serve pineapple side-up, drizzled with the remaining brown sugar glaze.