Willow Glen began as a marshy area with numerous Willow trees surrounding the Los Gatos Creek and Guadalupe River. It was drained in the early 1900's and planted with orchards. Later, houses and roads were built in the farmland and Willow Glen began to urbanize, with Lincoln Avenue developing as its downtown shopping area. In the 1920's a railroad was proposed to run through the middle of the community. Area residents joined together to successfully prevent the railroad from dividing their community.

In 1927 the area was incorporated as the town of Willow Glen. By the 1930's the growth of the community made it necessary to join the City of San Jose and in 1936, the town of Willow Glen ceased to be as it became a part of the City of San Jose.

During the 1960's, Willow Glen was once again faced with an attempt to divide its community with the proposal of an expressway that would run through the center of their neighborhood. Once again, the community joined together to stop this incursion.

Today, downtown is a bustling shopping district filled with shoppers, strollers and dogs walking up and down the sweeping tree-lined sidewalks.