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