1819-1887

On Christmas Eve 1869, the first train from Portland arrived in the small town of New Era, twenty miles away on the east side of the Willamette River. Benjamin Holladay, a driving force behind the road, was one of the passengers. A year and a half earlier, two railways had begun construction in Portland. One, on the west side of the river, was supported by attorney Joseph Gaston and Portland city officials, while the other had the support of the Central Pacific Railroad and Holladay. Competing for both traffic and a federal land grant, the two sides agreed that whichever company first built twenty miles of line would buy out the other. Holladay won the race and expanded the east and west side lines until his finances collapsed in 1873.

Born in 1819 in Kentucky, Holladay moved with his family to Missouri as a young boy. In Weston, Missouri, Holladay operated a store and a hotel, doing business with Indians in Kansas. He married Notley Ann Calvert when he was 23. After she died in 1873, Holladay married Esther Campbell.

When the Mexican American War broke out in 1846, he supplied U.S. Army General Stephen Kearny's forces. After the war ended 1848 Holladay bought surplus army supplies at bargain prices, and over the next several years he sold these supplies in Utah and California. In 1862 Holladay bought the Overland Mail Express, whose owners were in debt to him. He expanded the company and by 1864 controlled most of the stage and freight traffic between the Missouri River and Salt Lake City. Holladay also had a federal mail contract worth nearly one million dollars annually.

Holladay's business began to suffer in 1864. Recognizing that the growth of railroads threatened the stage business, Holladay sold his stage coach line to his competitor, Wells Fargo, in 1866 for $1,500,000 and moved to Portland.In Portland he entered the railroad business in 1868. Holladay's Oregon and California Railroad reached the towns of New Era in 1869, Albany in 1870, and Roseburg in 1872. His line on the west side of the Willamette reached Hillsboro in 1871. Then, in 1873, Holladay began to default on loans. Known as an extravagant spender, Holladay owned numerous mansions on both coasts and had over-extended himself financially. He lost his railroad in 1876, and died in Portland in 1887.

In Portland he entered the railroad business in 1868. Holladay's Oregon and California Railroad reached the towns of New Era in 1869, Albany in 1870, and Roseburg in 1872. His line on the west side of the Willamette reached Hillsboro in 1871. Then, in 1873, Holladay began to default on loans. Known as an extravagant spender, Holladay owned numerous mansions on both coasts and had over-extended himself financially. He lost his railroad in 1876, and died in Portland in 1887.