Start by organizing all your ingredients on a clean workspace. Use a knife to cut your cheese into uniform cubes, about half an inch thick, which will serve as the sturdy base of your tree. Wash the grape tomatoes and pat them completely dry with a paper towel to ensure they do not slip on the skewers.
Take a slice of turkey pepperoni or beef salami and fold it in half, then fold it again into a small accordion shape or a triangle. This creates volume and mimics the layered branches of a Christmas tree. If your slices are very thin, you can use two slices per skewer to make the tree look fuller.
Thread the ingredients onto the wooden skewer starting with the mozzarella pearl at the very top. Follow this with a green olive, another folded piece of meat, and a grape tomato. Finally, push the skewer into the cube of cheddar cheese at the bottom, which acts as the tree trunk and keeps the skewer standing upright or lying flat securely.
Tuck a small sprig of fresh rosemary into the top of each skewer, right next to the mozzarella pearl, to give it an authentic pine tree appearance. Place all the completed skewers on a large serving platter. In a small bowl, mix the olive oil and dried oregano, then lightly drizzle this over the skewers for a glossy finish and a boost of herbal aroma.