The Vinyl Skyway was founded in 2003, when neighbors Michael Hayes and Andy Santospago began hanging out and playing songs together in Watertown, MA. Both had just parted ways with their bands (Lemonpeeler and Jr. Corduroy). Eventually, the two decided to start anew, and in 2005 they released a self-titled debut that wound up in the hands of Nic Harcourt which he played on KCRW's "Morning Becomes Eclectic". A bit of press with NPR's All Songs Considered, and some positive feedback from Nick Hornby (High Fidelity) were also helpful. Boston Phoenix rock critic Jonathan Perry describes the album as "gorgeous songs about faith and betrayal, street-corner blues and early-morning benders that would sit nicely alongside Wilco's "Being There," rating it as one of the best local Boston releases of the year.

Late in 2005, Hayes and Santospago would head to the west coast for a series of shows with drummer Booth Hardy and bassist Rob Pevitts (formerly of Lemonpeeler). A combination of chemistry and compelling new material kept the four together bi-coastally. In early 2006, producer Bil Bowen took his band to Kissy Pig studio in Allston, MA, where they were introduced to proprieter Karl Mogensen and his enormous Neve console. Over the next nine months, they added keyboardist Dave Lieb and completed the recording of their sophomore album. When it was finished, the Boston Globe published a cover story previewing From Telegraph Hill with comparisons to Fleetwood Mac, the Thrills and the Pernice Brothers. Separately, the Globe's review referred to it as a "headphone record of exquisitely crafted pop." It would be referred to as a breakthrough, and some called it 2007's best independent rock release.

Unfortunately, the Vinyl Skyway was spending money on making records at a time when the music industry was unravelling, and taking money away from the artist. The 69 cent song put a new spin on the term "struggling musician". In 2008, the band fell into a three year period of hiatus, broke from a lack of financial success, yet moving on in life to the joy and fulfillment of family. Both Hayes and Santospago continued to develop new material while becoming fathers.

In 2011, Hayes and Santospago reunited with a successful kickstarter campaign which ignited their third album entitled "Return of the Dead Surfer." The album was promoted only on Facebook and sold exclusively on bandcamp. NYC college radio station WFMU picked up the album thanks to DJ Pseu Braun, whose show "Pseu's Thing with a Hook" provided generous airplay. The album is currently being re-released in deluxe edition format on bandcamp.

Santospago writes, sings harmonies, plays lead guitar and a bevy of other instruments. Hayes, who recently moved his family from Boston to Chicago, has operated as songwriter and co-producer for all releases, performing lead vocals, harmonies, rhythm guitar and some piano. Both attended the Berklee College of Music, and continue their songwriting partnership from afar with plans of recording new material for release in 2014. The band lineup has changed several times since 2004, and currently features keyboardist Lieb, Mickey Vershbow (Plumerai/To the Wedding) on drums and Marc Hickox (Paddy Saul) on bass. Hickox and drummer Andy Plaisted comprised the rhythm section for the Dead Surfer sessions in 2011.