Preheat the oven to 350F and add a sheet of parchment paper to a baking tray. Then, pit the cherries and cut them in half. Add the cherries to the parchment lined baking tray and pour on the maple syrup and vanilla. Use your hands or a spoon to mix all the ingredients together until the cherries are evenly coated. Then, add to the oven and bake for 20-25 minutes. 

While the cherries are roasting, make the pineapple layer. Add the pineapple, yogurt, and maple syrup to a blender and blend until smooth. Then, add about 1 Tbsp of the pineapple filling to each popsicle mold. Add the mold to the freezer for 15-20 minutes while the cherries finish roasting and cooling.

Once the roasted cherries have cooled a bit, pour them into a blender making sure to scoop in any syrup left on the parchment paper. Blend the cherries until smooth.

Take the popsicle mold out of the freezer and add 1 Tbsp of the blended roasted cherry filling to each mold. Then, top with the remaining pineapple and cherry filling until each mold is full.

Place the lid onto the popsicle mold and add in wooden popsicle sticks. Then, place the popsicle mold in the freezer for 6-24 hours until the popsicles are frozen.

Remove the mold from the freezer and quickly run the bottoms of the mold under lukewarm water to help with popsicle removal. Once the popsicles have been removed enjoy immediately as they will melt fast. Enjoy!