Preheat the oven to 400°F.
In a small bowl, whisk together 2 tablespoons of olive oil, balsamic vinegar and 1/2 teaspoon of the salt. Set aside.
In a large bowl, add the squash, 2 tablespoon of olive oil, rosemary, brown sugar, 1 1/2 tsp salt, and pepper. Mix well until all the squash is coated. Place on a baking sheets lined with tin foil.
Roast for 40 minutes, until tender. At 20 minutes in, toss the cubes so they brown evenly.
Take out of the oven and sprinkle the pistachios and cherries over the squash. Drizzle with the vinaigrette and allow it to cool and absorb the dressing for about 10 minutes.
Transfer to a serving dish and serve warm.