Directions:

Preheat oven to 375 degrees.
Using fingers, rub off the outer most white peel off garlic (don't worry about leaving a lot of peel), roasted garlic peels easily once it is cooled).
Place head of garlic in center of a six-inch square of foil. Drizzle olive oil over the top of garlic. Wrap foil around garlic and bake for 45 minutes.
Boil potatoes for 15-20 or until potataoes are tender when pierced with a fork. Drain.
Remove garlic from oven when done, open foil, and allow to cool.
Peel garlic by squeezing cooled cloves into a large mixing bowl. Puree garlic with 1/2 butter and milk, using hand blender or mixer.
Add potatoes and remaining butter and milk and mix until smooth.
Add salt and pepper to taste.