Songfacts®:

• This song is off Cinderella's second album, Long Cold Winter. The lyrics offer a glimpse of perseverance, loneliness, and doubt that come upon realizing your dream of success. Maybe it's not always what it seems?
  
  In our interview with Cinderella's Tom Keifer, he intimates that his songs are not about specific people or occurrences, but "more about emotions that are more cumulative or an average of a lifetime."
  
  Evidence "Gypsy Road." The lyrics in this song cannot be lived in a week, month, or even a year. They are a composite of Tom's memories of a life on the road. The hotel rooms, the overnight rides on the tour bus.
• Tom Keifer had wanted to move forward with a blues-rock sound with this track even though the band had a glam rock aura that was associated with the late 1980s sound. The chord structure to "Gypsy Road" is more detailed than the typical two note power chord associated with the average glam rock band. It's a combination of Blues style open chords and barre chords that move on a faster pace than the lyrics. You can close your eyes and envision this song being played on acoustic guitar with a slide.
• There exists a live video of the band performing Gypsy Road at The Moscow Peace Festival in 1989. What's interesting to note of the live versus studio version is the ballad like synthesized intro and first verse sung by Keifer that lasts 1 minute 46 seconds before the rest of the band kicks in.