Preheat the oven to 375˚. Slice off about 1/4 inch from the top of the garlic head. Place cut-side up on a piece of foil. Top with the olive oil and a pinch of salt; snap a rosemary sprig in half and place on top of the garlic. Wrap in the foil. Roast until the garlic is soft and golden, about 1 hour. Carefully open the foil and let the garlic cool slightly, then squeeze the cloves out of the skin; discard the rosemary.
Meanwhile, butter a 2-quart baking dish. Smash the remaining 2 garlic cloves; add to a large pot along with the potatoes and the remaining 3 rosemary sprigs. Cover with cold water by 1 inch and season generously with salt. Bring to a boil, then reduce the heat to a simmer and cook until the potatoes are tender, 15 to 18 minutes. Drain well; discard the rosemary sprigs.
Increase the oven temperature to 450˚. Press the potatoes, boiled garlic and roasted garlic through a ricer or food mill back into the pot. (Alternatively, return the potatoes and boiled garlic to the pot along with the roasted garlic and mash with a potato masher.)
Fold in the butter until melted. Gradually stir in 3/4 cup milk until smooth. If the potatoes still seem thick, gradually add the remaining 1/4 cup milk as needed. Season with salt.
Transfer the mashed potatoes to the prepared baking dish. Bake until browned on top, 30 to 40 minutes.
Tools You May Need
Photograph by Ralph Smith
Tools You May Need
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