Like the Battle Ax in Bayfield County, Ashland County also had its own railroad. The Minneapolis St. Paul & Ashland Railroad, or Peerless as it was known, was a product due mainly to the strong promotion by Ashland pioneer, Charles A. Pratt. A vote was taken and the road was approved, Ashland County bonding $68,000 to build the road. Construction began in 1896 and was completed to Chequamegon Junction in 1897, a distance of about 23 miles. Its president was S. G. Cook who owned the Cook mill in Ashland, and one of the directors, J Cochrane, was the president and secretary of the Keystone Lumber Company of Ashland, so one can assume that it was intended to be nothing but a logging road in the first place. The idea proposed to the taxpayers was to have a railroad run from Ashland to the Twin Cities via Hayward, Shell Lake and St. Croix Falls, but the main line never made it past Chequamegon Junction, a spot where it joined the Duluth South Shore and Atlantic tracks. Here the DSS&A put up a fight to stop the road from crossing its tracks. Plans were made to go over or under the DSS&A but never materialized. According to the historian Guy M. Burnham, the railroad never hauled a passenger to Ashland, but was strictly a logging railroad.

The railroad began near the Shores mill on Ashland's waterfront and was used to haul  logs to the Cook mill which was located down from Prentice Park. After about two years the logs along the line were cut and a 22 mile long spur was then built from a point east of Moquah to near Port Wing at a place called Ole Olson. This spur was for the purpose of hauling Weyerhaeuser logs to the Cook mill. The spur apparently went under the  WB&IR at Bena. Weyerhaeuser & Rutledge, who held 316 of the 320 $1,000 bonds, forced the company into bankruptcy and had a Weyerhaeuser man, E. L. Ainsworth appointed as trustee. Its peak trackage was reached in 1902 when 46.5 miles were reported. On at least one occasion, logs were brought to Ashland and rafted to a Washburn mill. The line was abandoned in 1906 with the exception of a 1.76 mile stretch on the Ashland waterfront which remained open until 1911 to serve the Lake Superior Lumber & Box Company. The bonds, which eventually totaled $120,00 to $140,000 were finally retired about 1918.

At the time of abandonment, lumber prices had dropped so drastic that a full loaded lumber train was left in the vicinity of Hoist Lake. The  local residents cut it up for scrap iron during WWI and the CCC's eventually salvaged some of the logs for use in there projects. In the 1960's many logs were salvaged from the bottom of Hoist Lake and cut into lumber.