1. Heat oven to 250'F. Peel beets and cut into 1/4-inch cubes. In separate bowls, toss beets and garlic each with 1 T olive oil and 1/2 t pepper. On rimmed baking sheet, place beets on one side and garlic on the other; cover tightly with aluminum foil. Roast 25 minutes or until tender.
2. Meanwhile, make croutons: Cut bread into 1/4-inch pieces. Brush with olive oil; season with salt and pepper. Arrange on another baking sheet and place in oven until toasted-about 15 minutes.
3. Prepare Sherry Vinaigrette.
4. Just before serving, in large skillet, heat 1 t olive oil over high heat. Add chicory, beets, and garlic and saute just until chicory starts to wilt-no more than 1 minute. (If there is not enough room in skillet, do this step in 2 batches.) Add 1/4 C Sherry Vinaigrette to salad and toss. Divide onto 4 serving plates; garnish with croutons. Serve immediately, passing remaining Sherry Vinaigrette separately.
Sherry Vinaigrette, In small bowl, whisk together 1/2 C sherry vinegar 1/4 C extra-virgin olive oil, 2 cloves garlic, finely chopped, and 2 t finely chopped fresh rosemary until well combined.