Leavenworth, originally called Icicle Flats, was first settled in about 1885 as a trading post. The first white settlers came to trade with the Wenatchi, Chinook and Yakima tribes. The native tribes had long used the confluence of the Wenatchee River and Icicle Creek as a salmon fishery and hunting ground.

With the completion of JJ Hill’s Great Northern Railway in 1893, Leavenworth, as Icicle Flats was now known, began to come into its own as a northwest frontier town. Platted in the same year by Captain Charles F. Leavenworth, the town became a powerful timber center. The Lamb-Davis Sawmill was one of the largest in the country. Proximity to The Great Northern Railway brought many jobs to Leavenworth. At the time Leavenworth was first mapped in 1904 it had a population of around 700.

The town thrived until The Great Northern Railway pulled out of Leavenworth. The new route, which would be subject to snow closure less often, bypassed the town, causing the timber companies based along Icicle Creek to fail. The town languished nearly to extinction until the early 1960’s when town leaders came up with a plan to convert the town’s primary source of income to one based in tourism.​

Town leaders and business owners drew up a plan to transform the appearance of Leavenworth from frontier town to Bavarian village. In addition to the change of appearance, community leaders came up with a series of festivals, that once established and expanded upon, would be eventually responsible to bring over 1 million visitors to the village each year!