The Cranberry Lumber Company was originally located in East Saginaw Michigan. When the logging began to dwindle in Michigan, they looked elsewhere for timber and in 1899 they began to log 200 million feet of pine in the Herbster area. The would purchase the rights to much more pine as time went on. The company’s headquarters were in Ashland and the camp headquarters was at the mouth of the Cranberry River and Cranberry was the name of the camp and settlement that grew up around it. Herbster came about after the saying "go see Herbster", for anyone wanting to know where to get their mail. Billie Herbster was the camp cook who handled the mail, and the name stuck; Herbster, the town, being named after him*.

The first logs were cut close to the Cranberry River and floated down to the lake where they could be towed to the mill. In early 1890 the company purchased the tug "Bennett" for $11,000, reputed to be the most powerful tug on Lake Superior. In the spring, construction by the Cranberry Lake Company began on five miles of standard gauge railroad to better provide transportation for getting the logs from the woods to the lake.  The first locomotive was placed on a scow in Ashland and towed by the "Bennett" to Herbster. Eventually this railroad would extend almost to Siskiwit Lake to the east, down "Old 13" from the Buckley Road to new Highway 13 to the west, down into the Flag River to the southwest, and south as far as southwest of Lenawee Lake. The log dump for the railroad was located close to the bridge in Herbster on "Old 13"

As an example of the size of the trees in the area, a tree was felled in February of 1891 that scaled 4,599 feet and was cut into 8 logs.

In the late summer of 1890, the Cranberry Lumber Company moved its offices from Ashland, WI to Duluth, Minnesota. To give you an idea of the size of the operation, the company received a shipment of 16 carloads of camp supplies in Ashland in the late fall of 1890.

In 1894, the Cranberry Lumber Company leased the R. A. Gray mill in Duluth. Also that year, another company, the Siskiwit Lumber Co., which owned a large tract of land east of the Cranberry holdings, used the Cranberry River Railroad to log their land. These logs were transported to the huge Merrill & Ring mill in Duluth, along with a large contract of logs by the Cranberry Lumber Co. for Merrill & Ring also.

In early 1895, the headquarters camp and engine-house in Herbster burned down and later that year the railroad and logging operations were taken over by Simpson Gould & Co. At the time there was 16 miles of railroad, with 2 locomotives and 50 cars. Sam Simpson was in charge of the operation. He estimated in 1898 that there was one billion feet of standing timber in the area of Northern Bayfield County where he was logging and intended to cut 50,000,000 feet per year.

By 1898, the timber was running out in the area. (Simpson was not the only logger in the area) No summer logging was done this year and the winter of 1898-1899 was the last year of operation. In November of 1899 the railroad was removed.

"Cranberry Lumber did acquire a considerable amount of timber land in northeast Minnesota but ultimately sold most of it or paid other companies to cut it for them. Cranberry Lumber had only two of its own operations in Minnesota. The most substantial was near Fond du Lac MN, where they had an annual cut of 35,000,000 feet each year for several years. Those logs were floated down the St. Louis river to Duluth Mills also.**"