I love the idea of a simple potato mash that still tastes sinful without all the butter and the cream. The amber honey and balsamic vinegar in this recipe are both just tossed in at the end, but they seriously make the recipe! —Jacqueline Russo
Place rack in upper and lower third of the oven. Preheat oven to 350 degrees F.
Wash sweet potatoes and squash. Cut acorn squash in half and remove seeds. Cut potatoes into uniform size pieces (in half is fine). Slice bottom 1/2-inch from garlic but try to keep intact.
Coat potato pieces, squash halves, and bottom of garlic with a bit of olive oil. Wrap the garlic and each potato in aluminum foil with 1/2 a sprig of rosemary each. Lay squash pieces cut side down on a baking sheet with 1/2 a sprig of rosemary underneath each. Bake for approximately 45 minutes, or until soft enough to scoop.
Once cool, discard rosemary and scoop fleshy parts of squash and potatoes into a large skillet. Squeeze garlic cloves out and mix to combine.
Over medium heat, add 1/2 cup of apple cider at a time and stir or mash with a potato masher.
Stir in honey and balsamic vinegar, and season with flaky sea salt and fresh ground pepper to taste.
At this point it's ready to serve, but if you're preparing ahead you can always reheat it over the stove and add a bit more apple cider to soften it up again.