Preheat oven to 350°F.
Toss beets with olive oil and roast in a baking dish for about 1¼ hours until tender.
Allow beets to cool, then peel and quarter them.
Peel oranges and remove white membrane, then segment over a bowl to catch the juice.
Trim fennel bulb, quarter, and slice thinly.
Combine beets, orange segments, sliced fennel, reserved orange juice, orange-infused olive oil, red wine vinegar, salt, and pepper in a large bowl and toss gently.
Serve salad on lettuce leaves and top with optional fresh herbs, toasted almonds, or goat cheese if desired.