| Achievement | How to unlock
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| Althea (25 points) | Completed Althea's story.
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| August (25 points) | Completed August's story.
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| Bertha (25 points) | Completed Bertha's story.
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| Carnivale (25 points) | Completed the Runciter's Circus vignette sequence.
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| Cassady (25 points) | Completed Cassady's story.
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| Dehaaya (25 points) | Completed Dehaaya's story.
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| Dupree (25 points) | Completed Dupree's story.
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| Fidelina (25 points) | Completed Fidelina's story.
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| Franklin (25 points) | Completed Franklin's story.
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| Friend of Mine (25 points) | Completed the Devil vignette sequence.
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| Got Your Kicks (25 points) | Hitchhiked along Route 66.
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| Jimmy (25 points) | Completed Jimmy's story.
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| Little Ben (25 points) | Completed Little Ben's story.
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| Mason (25 points) | Completed Mason's story.
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| Quinn (25 points) | Completed Quinn's story.
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| Ray (25 points) | Completed Ray's story.
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| Rocio (25 points) | Completed Rocio's story.
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| Rose (25 points) | Completed Rose's story.
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| Shaw (25 points) | Completed Shaw's story.
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| Storyteller (50 points) | Completed your task.
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| The Beat Poet (25 points) | Met Cassady, the beat poet.
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| The Blues Singer (25 points) | Met Althea, the blues singer.
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| The Coal Miner (25 points) | Met Little Ben, the coal miner.
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| The Cowboy (25 points) | Met Ray, the cowboy.
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| The Curandera (25 points) | Met Fidelina, the curandera.
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| The Dustbowl Refugee (25 points) | Met Bertha, the dustbowl refugee
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| The Gambler (25 points) | Met Dupree, the gambler.
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| The Great War Veteran (25 points) | Met Mason, the Great War veteran.
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| The Hippie (25 points) | Met Rose, the hippie.
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| The Hobo Kid (25 points) | Met Quinn, the hobo kid.
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| The Migrant Worker (25 points) | Met Rocio, the migrant worker.
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| The One Who Went Upward (25 points) | Met Dehaaya, the one who went upward.
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| The Preacher (25 points) | Met Jimmy, the preacher.
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| The Pullman Porter (25 points) | Met Franklin, the Pullman porter.
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| The Sailor (25 points) | Met August, the sailor.
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| The Sharecropper (25 points) | Met Shaw, the sharecropper.
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| Where the Water Tastes Like Wine (50 points) | Found the place where the water tastes like wine.
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| Whip-poor-will (25 points) | Found the three whippoorwills.
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