Wash and dry the mini bell peppers. Slice off the tops and scoop out the seeds using a small spoon.
Carve jack-o’-lantern faces into each pepper using a small, sharp paring knife.
In a mixing bowl, combine cream cheese, shredded cheddar, chives, garlic powder, salt, and black pepper. Mix until smooth.
Use a spoon or piping bag to fill each pepper with the cheese mixture. Press the tops back on as lids.
Place the stuffed peppers upright on the charcuterie board.
Arrange the salami slices, crackers, grapes, cucumber slices, and pretzel sticks around the peppers.
Optional: Add festive toothpicks, extra veggies, or herbs for garnish.
Serve immediately, or chill for up to 2 hours before serving.