"I thought the people were going to hate me and think I was there to exploit their culture," Simon expressed to The Sunday Gleaner before revealing that by the end of his eight-week trip, he was embraced and accepted when everyone realised his "heart was in the right place".
The extraordinary photographer also revealed that his trip was due to a book contract he signed with music journalist and historian, Stephen Davis. The book, Reggae Bloodlines, which was published in 1977, was the first book published in America about the Jamaican culture, according to Simon.
This then lead to Simon starting a reggae programme called 'Reggae Bloodline' on a major radio station in New England, where he amassed a huge following over the show's 10-year span.
Simon's love affair with reggae music continued and the artist's second book, Reggae International was released in 1982.
After a 20-year hiatus, Simon was approached by a publisher to do another book and he returned to Jamaica in 2006, this time with his son, Willie, who had inherited his father's love for Jamaican culture.
The entire journey is summed up in Simon's photo exhibit at Puls8.
A small ceremony was hosted at Puls8 on Thursday night to launch the exhibit which will run throughout the month of March from 10 a.m. to 7 p.m. daily.
Having captured many priceless moments in reggae and some of the biggest names in the genre, Simon's photo exhibit is just a handful of the pictures from the acclaimed photographer's catalogue, which chronicles Jamaica's musical history.
The exhibit inspires patriotism as each picture is branded 'Jamaican' in print that may be invisible to the eye, but can definitely be perceived.
Toots Hibbert blessed the launch in a way only he could - with his soulful voice and infectious energy.
With only his acoustic guitar, the reggae stalwart delivered a short-but-sweet performance which bolstered the fact that the night did not only belong to Simon, but also to reggae.
Patricia Chin of VP Records also invited JaAnna, a reggae enthusiast from Japan, to give a brief performance. JaAnna obliged and sang two sweet renditions for the audience, accompanied only by her melodica.
Simon revealed that the pictures included in the exhibit are of the people he really cares about. He pointed out that there were no dancehall musicians featured in the exhibit as he is not a fan of the genre.
"I have to admit that I've developed a prejudice against dancehall. It's not reggae to me. I stay away from the really homophobic, sexist, racist, violent stuff. I only want the peace, love and understanding," Simon mused, adding that his son did not inherit these sentiments as he is big dancehall fan.
Simon admitted that it is harder for him to find the reggae music he really loves nowadays but he sees a bright future for reggae in artistes like Tarrus Riley and Etana, both of whom are featured in the exhibit.