Cook the bacon in a skillet over medium heat until crisp, about 10 minutes. Transfer with a slotted spoon to a paper towel-lined plate. Reserve the drippings.
Make the dressing: Combine the tomato paste, vinegar, sour cream, shallot, tarragon, sugar and 1 tablespoon bacon drippings in a medium bowl; whisk well. Add the olive oil in a slow stream, whisking until emulsified. Whisk in 2 to 3 tablespoons water to make the dressing thin enough to drizzle. Season with salt and pepper.
Arrange the iceberg wedges on a platter and drizzle with the dressing. Top with the tomatoes and bacon.