McGregor had a keen interest in railways since childhood. From the 1980s he started collecting railway memorabilia, including several vintage railway carriages which he restored on his property, "Ruwenzori", near Mudgee NSW. By 1989 he had collected so much he decided to sell some and opened a stall called "Off The Rails" at the now closed "Chelsea House" antiques emporium in Camperdown, New South Wales. Branches were later opened at Sydney's Central Railway Station and in Balmain. In 1992 a new "Off The Rails" shop was opened in Newtown. It moved again to a larger shop and restoration workshop at Camperdown. The shop closed in 1999 and "Off The Rails Collectables" now operates as a mail order business and from his Mudgee property. In 2005 McGregor opened his country property as tourist accommodation. "Ruwenzori Retreat" is perched on the Great Dividing Range north of Mudgee and is made up of a collection of 9 vintage carriages, a number of which date back to the 1890s and the 3 main carriages are restored as the luxury guest accommodation. The 50 acre property also has station buildings, track, signals, a plethora of memorabilia and a network of bush tracks. Ruwenzori Retreat has featured on TV programs such Getaway, Today, World's Most Extreme Homes, and many others. McGregor and his Ruwenzori railway collection have also appeared on the ABC TV program "Collectors". In 2007 McGregor began hosting Railway Adventure tours in conjunction with Sydney-based travel company Renaissance Tours to a variety of destinations in Australia and overseas including Vietnam, Eastern Europe, Japan, India, New Zealand and North Queensland. In 2012 he established his own travel company 'Railway Adventures' Page text., dedicated to providing rail-themed tours in Australia and overseas. Since then he has hosted over 150 tours to destinations far and wide, together with a growing band of tour leaders and hosts. McGregor has turned his love and hobby of trains into a successful career. His fascination of all things trains and the fascination of how rail has impacted our current world, essentially sparked the success of "Scott McGregor's Railway Adventures". Travelling by rail has grown to yet again become such a wonderful way to experience and witness the country that you are visiting. This is one of the main reasons that McGregor has been able to harness such an incredible base for this business and give people such a personal experience that they will never forget.