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The Road Not Taken was the second album released by country music group Shenandoah and their most successful album to date. Of the six singles released from 1988 to 1990, all charted within the top ten and three of those, "The Church on Cumberland Road", "Sunday in the South", and "Two Dozen Roses" were number 1 songs on both the U.S. and Canadian country charts. Also included on the disc is "She Doesn't Cry Anymore", a single from the band's self-titled debut from 1987.