Preheat oven to 400 degrees. Place tomatoes, red pepper, and anaheim pepper chunks on a large sheet pan prepared with cooking spray. Spray lightly with cooking spray, and season with salt and pepper. Roast in the oven for 40 minutes. Remove from oven and cool.
Combine tomatoes, peppers, cucumber, and shallot in a blender. Puree until smooth, at least 2 minutes. With motor running, add vinegar, water, and 2 tsp. salt.
Chill at least 6 hours, or overnight.
Before serving, adjust the seasonings by adding salt or vinegar to taste. If soup is thick, add a few tablespoons of water to loosen it up. Serve in your favorite bowl, or shot glasses. Garnish with fresh basil or cilantro
Notes
Adapted from an original "award-winning" recipe from Ron Snitker