Walter C. Willson, the man who built up the town of Newcastle and changed its name to Webster City, realized that the city on the prairie was growing. The supply of timber was not going to be sufficient to allow for heating the homes with wood much longer. Some small coal mines were developed at Tunnel Mill and Bone’s Mill, but they did not produce the large quantities of coal that would be needed.

Willson, who earlier had acquired large holdings of coal lands near Lehigh along Crooked Creek, conceived the idea of building a railroad from some point along the Illinois Central (then called the Iowa Falls and Sioux City Railroad) line to Lehigh. Coal could be hauled much cheaper and faster than the current method of hauling the loads by team and wagon. Willson was familiar with railroading, having graded and constructed the line from Iowa Falls through Webster City and on to Storm Lake in 1869. He determined that the simplest solution would be to build a short line south from the Illinois Central tracks to Lehigh.

To find the best route, Willson started walking north from Lehigh, noting the need for bridging and places where cuts would have to be made. He arrived at Border Plains, an early settlement located west of Homer. Then he continued north to a junction with the main line between Webster City and Fort Dodge.

To raise funds, Willson went to Milwaukee, Wisconsin, and met with J. H. Judd, George Burnham, C. D. Burnham, and John Q. Burnham. These four men agreed to invest money in the new corporation, the Crooked Creek RR and Coal Company. Then on December 21, 1875, he traveled to Des Moines and filed the articles of incorporation with the Secretary of State. Capital stock was $500,000, issued in 5,000 shares with par value of $100 each. The directors signing the original articles were W. C. Willson, Jacob M. Funk, and S. B. Rosenkrans. The railroad was no longer Willson’s dream. He was now authorized to lay rails, sink mines, and haul coal.

The Hamilton Freeman reported on October 4, 1876, that the first six miles of track had been "ironed" and that the engine and rolling stock were already there.

A later news article in the Hamilton Freeman of January 10, 1877, reported that the original intent was to put down a wooden track, costing not over $5,000 per mile. This idea was soon abandoned, and instead a narrow gauge line of fish-plate iron was laid over the nine-mile route. A town was laid out at each end of the line. The junction with the main line was called Judd (for J. H. Judd), and Lakawana was the name given to the southern terminus.

The newspaper account continues by describing Judd as having a good depot, telegraph office, and 57 acres of land on which people were encouraged to settle. Lakawana (now Lehigh) was reported to have only one dwelling on October 1, 1875, but by January 10^th boasted 35 houses, stores, shops, a hotel, and mills. About 100 miners had been hired to work the mines.

To transfer the coal, the Illinois Central laid a track parallel to its main track but elevated above it. This was necessary so that the narrow-gauge coal cars would be at the same level as the standard gauge cars. A "Wye" was constructed that allowed the Crooked Creek train to travel north, take a curve west, then back up parallel to the Illinois Central. Men were hired at 10 cents per hour to shovel the coal from the Crooked Creek cars to the Illinois Central cars. After the cars were unloaded, the train backed up until it cleared the "Wye" and then took a curve back south to Lakawana.

At first, the tracks stopped at Chance and McClure Mines on the east side of Lakawana. The depot was located in a large brick building south of a wagon bridge across the Des Moines River. In 1879, a 370-foot wooden bridge spanned the river and provided access to the Crooked Creek mines.

The entire line was now complete. Ten bridges were required. The entire cost of construction was $59,815. The locomotive cost $12,630; a passenger car, express car and 33 freight cars totaled another $22,310.

The Crooked Creek RR continued operation for four years, one month, and two days. It was a real success. Willson decided that he would rather bring the coal directly into Webster City and convert the narrow gauge line to standard gauge. To effect this he organized the Webster City and Southwestern Railroad, which he incorporated on October 31, 1883. The directors of this railroad were W. C. Willson, Jacob M. Funk, and S. B. Rosencrans. It used the route from Lehigh to Border Plains but then turned east to pass though Brushy and Flugstad and on to Webster City, a distance of 13 ½ miles. A new depot and roundhouse were constructed where the new Hy-Vee grocery store is under construction. The depot is pictured with this story.

The official name of the road was Webster City and Southwestern RR, but the local people continued to call it the Crooked Creek RR. On August 1, 1900, tragedy struck when Willson, President and General Manager, was helping unload a car of slag. The car toppled over and crushed him. His funeral had the largest attendance of any funeral in the history of Webster City. Special trains transported miners from Lehigh and friends of Willson from Fort Dodge.

After Willson’s death, Jacob Funk took over as President. When Funk died in 1903, Willson’s son, Frank E. Willson took over as Secretary and General Manager. A 1907 letterhead lists C. E. Burnham, Pres.; F. Paul Stone, Vice Pres.; C. L. Burnham, Sec.; L. A. McMurray, Treas; and F. E. Willson, General Manager. The Webster City Journal reported on December 1, 1910, that the Fort Dodge, Des Moines and Southern, an interurban line, had purchased the Crooked Creek RR and the Webster City and Southwestern RR for $112,000. This transferred the right of way, the rolling stock, and the terminals to this line.