Preheat oven to 400° F. Cut top 1/2 inch off the garlic heads and place on a piece of foil. Drizzle with a small amount of olive oil. Wrap loosely with foil and bake 1 hour. Cool slightly. Reduce heat to 350° F. Peel and quarter potatoes. Place in a large pot and cover with cold water. Bring to a boil over high heat. Reduce heat and cook potatoes for 20 to 30 minutes, until they are soft when pierced with a fork. Heat milk and butter to have ready. Drain potatoes; return to the heat and shake them to evaporate any excess water. Remove from heat. Squeeze garlic into potatoes. With an electric mixer, mash potatoes only until smooth then beat in only enough of the milk mixture until they are desired consistency (do not over beat). Fold in the cheese. Place the potatoes in a 13 x 9 x 2-inch baking dish. Bake covered for 10 minutes.
<em>*To make ahead of time, cover and refrigerate the baking dish until needed. Preheat the oven to 350° F. Bake potatoes, covered, for 35 to 45 minutes or until hot.</em>
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