| Achievement | How to unlock
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| - Completed Althea's story.
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| - Completed August's story.
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| - Completed Bertha's story.
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| - Completed the Runciter's Circus vignette sequence.
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| - Completed Cassady's story.
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| - Completed Dehaaya's story.
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| - Completed Dupree's story.
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| - Completed Fidelina's story.
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| - 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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| - Completed Little Ben's story.
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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 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 Great War Veteran (25 points)
| - Met Mason, the Great War veteran.
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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 Pullman Porter (25 points)
| - Met Franklin, the Pullman porter.
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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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