Pat the pork chops dry on both sides. Add the rosemary, salt, pepper, and garlic. Rub it all in with your fingers. Place the pork chops in a zipped lock bag or plastic (or glass) storage container.
Refrigerate and marinade for at least 3 hours and up to 24 hours.
Let come to room temperature prior to grilling. While the pork chops are coming to room temperature, begin the pumpkin side dish.
PUMPKIN + APPLES
Preheat oven to 400 degrees F.
Line a baking sheet with foil or parchment paper. Place the pumpkin and apples in the center of the sheet. Drizzle on the olive oil and sprinkle on the salt and pepper. Use your hands or a spoon to toss and coat evenly. Spread out the pumpkin and apples in an even layer. Add on some fresh sage leaves and the ground cinnamon. When oven is heated, place the baking tray on center rack of oven.
Roast for 20 minutes, turning once. Add in the cranberries and use a spoon to combine and toss with the squash and apples. Roast 10 more minutes. It won’t take long for them to split open and release their juice, so may be ready even sooner.
While the pumpkin mixture cooks up, prep the pork chops.
When ready to grill, add some oil to the grill pan (or a skillet) over medium high heat. If you are using a grill pan, you will need to cook the pork in batches (if the chops are too crowded in the pan, the chops will steam and not sear properly). Place the pork chops on the grill. Cook on the first side for 3-4 minutes, until the pork chop easily releases from the grill.
Flip and cook on the other side for another 3-4 minutes (the cooking time will vary based upon your grill pan temperature and the thickness of your pork), until the pork reaches 135 degrees F on an instant read thermometer (the pork does continue to cook and the temperature will keep rising as it rests).
Pork chops are ready when the juices are a little pink, the pork is just firm to touch, and the center is a little rosy.
Place the pork chops on a platter, cover with foil paper, and leave it to rest for 8-10 minutes.
In a small bowl, whisk together 1 tablespoon olive oil, apple cider vinegar, maple syrup and cinnamon to make vinaigrette. Set aside. You could also make the dressing by adding all the ingredients to a mason jar. Shake well until all combined.
Remove pumpkin baking sheet from the oven and set aside.
Serve on the side with the pork chops. Serve the pumpkin side dish warm or room temperature.
Drizzle on the dressing as soon as you are ready to serve it. Add some fresh sage leaves or rosemary spring to serving platter. Enjoy!