Williamson attended Wake Forest-Rolesville High School in Wake Forest, North Carolina. He played for the school's baseball team as a pitcher, and was rated the best pitching prospect in the state of North Carolina.[1] He chose to enroll at Wake Forest University to play college baseball for the Wake Forest Demon Deacons. He redshirted as a freshman, and played for Wake Forest as an outfielder.[2] The Boston Red Sox chose Williamson in the 46th round of the 2011 MLB Draft, but he decided to return to Wake Forest for his senior year.[1]

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