This fashionable home built for Isaac Woolen in 1876 is an exceptionally intact example of Italianate residential architecture. Together with the Atkinson House, its immediate neighbor, it forms the strongest element in a row of noteworthy houses lining Main Street at the north end of town.

The Woolen house sheltered two of Ashland's most prominent citizens between 1876 and 1892.

Isaac Woolen came to Jackson County before 1860 and farmed in the Bear Creek Valley for fifteen years. At the age of 54, he married for the second time and purchased land in Ashland on North Main Street. In 1876 he constructed this large house on the hill for himself, his wife and their daughter.

Woolen became one of the first Ashland townspeople to bring water directly to the house when a water pipe was installed from the West Ashland Ditch to the house in 1878.

In March of 1880 the Woolens sold half of their lot to W. H. Atkinson and used the money to finance a year-long trip to San Francisco. The family returned to Ashland and decided to move to a smaller house.

Woolen sold his home to Captain Thomas Smith who had been born in Kentucky in 1809 and arrived in the Bear Creek Valley in 1851. He farmed south of Ashland on a Donation Land Claim, and at 75 years of age, decided to give up his ranch and move into Ashland with his wife Margaret and their child.

Smith represented constituents in the territorial legislature for one term and was later elected to the State Legislature for two terms. He died in his home on North Main Street in 1892 at the age of 83.

Adapted from the NRHP nomination submitted in 1979.