2 pounds cubed, peeled pumpkin
8 medium potatoes, peeled and cubed (about 2 pounds)
3/4 cup milk
8 tablespoons butter, softened
1 teaspoon salt
1 tablespoon olive oil
1 teaspoon ground pepper
Place pumpkin in a large saucepan; add water to cover. Bring to a boil. Reduce heat; cook, uncovered, for 20-25 minutes or until tender.
Meanwhile, place potatoes in another saucepan; add water to cover. Bring to a boil. Reduce heat; cook, uncovered, for 10-15 minutes or until tender.
Drain potatoes; return to pan. Mash potatoes, adding 1/4 cup milk, 4 tablespoons butter and 1/2 teaspoon salt. Add additional milk if needed to reach desired consistency. Transfer to a serving bowl; keep warm.
Drain pumpkin; return to pan. Mash pumpkin, gradually adding the remaining butter and salt and enough remaining milk to reach desired consistency; spoon evenly over potatoes. Cut through mashed vegetables with a spoon or knife to swirl. Drizzle with olive oil; sprinkle with pepper. Serve immediately.