Highpoint

County Road No. 186 known as the O. P. Stephenson Road was the first wagon road between Preston and Issaquah built in 1886. In 1905, John Lovegren started a sawmill two miles east of Issaquah at the top of the steep railroad grade. It wasn't long before people started to build homes near the mill and the small community became known as Highpoint. In 1922 the Highpoint Mill Company took over Lovegren's operations and continued to do business there until 1930.

The original wagon road from Highpoint to Preston crosses the creek and follows SE Highpoint Way to the Preston Cemetery. This was the route until 1914 when the road was realigned Highpoint to connect with SE Preston Way. In 1913 concrete bridges were constructed along Issaquah Creek for the new highway and one of these bridges still remains just off the exit at Highpoint.

In 1936, the highway was upgraded and the road between Issaquah and Preston was realigned. This new road follows somewhat in the path of the eastbound lanes of Interstate 90. The railroad was forced to realign it's right of way and moved it north closer to the creek. The grade still survives today as the Issaquah-Preston Trail.