The story begins on the Holly River in Braxton County in 1883. There the Holly River Lumber Co. operated a sawmill at Holly where the Oldlick Creek joins the Holly River. Needing a railroad connection to increase their market for their lumber they contracted with Joseph Fuccy of Sutton, WV to build a railway from the mill to the West Virginia & Pittsburgh RR (later Baltimore & Ohio) at Holly Junction, 5 miles away. Started in May of 1883 and finished in November, this railroad was built as a standard gauge line. Known as the Holly Lumber Company Railroad, this road operated until June 20, 1896, when the Holly River Railroad was chartered and assumed operations.
Prior to 1898 the Holly River RR opened a branch from Marpleton to Coalburg, the first coal branch on the railroad. And in 1898 a new logging branch was opened to Hackers Valley along the left fork of the Holly River. All these branches were built standard gauge. But this would soon change. In January of 1899 a narrow gauge (36" gauge) extension was built to Heckmer (named after George Heckmer, General Manager) along the right fork of the Holly River. A third rail was put down from Holly to Holly Junction to enable the narrow gauge to work most of the main line. In 1901 the extension was extended even further to Jumbo.
The Holly River and Addison Railway Company was incorporated on September 10, 1898, though it was not until May 15, 1899 that they were able to purchase the Holly River. This railroad was now owned by both John McGraw (owner of the Holly River Ry) and George Curtin , owners of most of the timber in the area. Why they took the name of Addison is unknown, the old town of Addison had changed its name to Webster Springs in 1897. The springs itself were known to have medicinal properties and a large hotel (the Webster Springs Hotel) was built that same year, but why did the railroad assume use of the old name? But the railroad built on ward to Webster Springs from a junction on the mainline at Diana, completing the line there on May 26, 1902. This was the end of the line for the next four years, and Webster Springs became a well known tourist destination at this time. By 1905 the company owned six locomotives, three passenger and two baggage cars, eleven box , five flat, 78 logging and 1 coal car. A 1919 equipment report lists the passenger equipment numbered as follows: #1 baggage car, # 2 combination car, # 3 to # 5 passenger day coach.