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Preheat oven to 400ºF. Wrap each beet in aluminum foil and place on a rimmed sheet pan. Bake until beets are barely tender when pierced with a small, sharp knife, about 1 hour. Let cool until easy to handle. Slip off beet skins. Halve beets and cut into 1/2-inch-thick half-moons.
Whisk vinegar, salt and pepper in a medium bowl. Gradually whisk in oil. Add beets, tomatoes and red onion and toss well. (Salad can be made to this point up to 1 hour ahead, or refrigerated for up to 8 hours.)
Just before serving, add watercress and toss again. Reseason with salt and pepper. Serve at room temperature or chilled.
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