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Preheat oven to 400 degrees. Line a small baking sheet with foil.
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Slice tomatillos, tomatoes, and jalapeño in half and spread on baking sheet.
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Drizzle with olive oil and salt.
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Roast for 15 minutes, then remove from oven and cool until room temperature.
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Once cooled, transfer to the blender. Make sure to add the juices in the pan as well.
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Add water, cilantro, lime juice, horseradish, Worcestershire, and hot sauce to the blender; blend until smooth.
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To assemble the drinks, rub one lime wedges around the brim of 4 tall glasses. Dip the rims of the glass into a shallow bowl of tajin seasoning.
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Add ice to each glass.
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Add 1 ounce of Prairie Organic Vodka to each glass, then fill ¾ of the way full with tomatillo juice; stir to combine. This can also be done in a cocktail shaker.
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Garnish Bloody Mary with celery stalks, bacon, and a skewer of shrimp and green olives, if desired.
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Serve immediately and enjoy!