In his early youth, he attended a private school in Richmond and later entered New London Academy in Bedford County, Virginia.
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On removing in 1868 to Franklin, New Hampshire, he entered the Franklin Academy, and after six months there, went to the New London Academy, subsequently Colby–Sawyer College.
Born near Churchville, Maryland, Webster received a classical training, and attended the Churchville Academy and later the New London Academy of Chester County, Pennsylvania.