Add a pinch of salt to a large pot of water and bring to a boil
Clean peppers and cut the tops off of each one. Remove seeds and membranes. Add peppers and tops to the boiling water and cook 3 minutes, until slightly tender. Add peppers and tops to a bowl of chilled water. Remove peppers once cool and use a small knife to carve each one like a jack-o-lantern.
Add half-and-half to a saucepan on medium heat and bring to a simmer. Continue stirring until half-and-half is reduce, about 10 minutes. Add room temperature cream cheese and continue stirring until smooth. Gradually add Cheddar and Peppadew cheeses until sauce is creamy.
Turn heat to saucepan off and begin adding macaroni while stirring to combine. Fill each pepper with two spoonfuls of macaroni and cheese, until full, and top each pepper with the top.