It all began on July 21, 1928 when Houstoun Waring, editor of the Littleton Independent, held a 40th anniversary celebration for the paper. The event was met with overwhelming support. The community, under the direction of Waring, decided to hold a celebration in 1929 commemorating the 100th anniversary of the birth of Richard S. Little, the founder of the Littleton community. The event was named "Homecoming" calling everyone who had ever lived or visited Littleton to come home.

Originally the Homecoming Celebration was set for May 12, 1929, on Richard Little's birthday, but when it was pointed out that railroad rates dropped in August and therefore "...people can come from great distances without much expense," the now traditional August date was set. The first Homecoming began with a play on Friday, August 1, 1929 titled "Adam and Eva" presented by the Littleton Dramatic Club to benefit the Littleton Hose company's Christmas Tree Fund.

The celebration continued with a ball game between the Littleton Hose Company and the Littleton Merchants. The "hose" boys invited local people who wished to decorate their cars or trucks to participate in the first parade. Though it rained on their parade, it didn't stop Mayor Louthan from riding on top of the town water wagon dressed in a Prince Albert costume and top hat. The Ford Essex, entered by the Bussard Motor Company was the first place winner in the car division and the winning truck was the Valore Hardware truck.

With the first parade, Mayor Louthan started the tradition of having a grand marshal of the parade. The selection is made by the parade committee and is a person who has made a significant contribution to the Littleton community.

In 1962, Homecoming Days was renamed Western Welcome Week. The Chamber of Commerce coordinated the expanded Western Welcome Week activities beyond the traditional Saturday Homecoming celebration.

In 1982 Western Welcome Week, was incorporated to Western Welcome Week, Inc. The board became responsible for setting policy guidelines, designating charities to receive grants from the proceeds, and appointing a chairman and co-chairman to organize the event each year.

Today, Western Welcome Week is an eleven-day celebration with over 40 events. The not-for-profit corporation has an office staff of two and is run by a 13-member volunteer working board, an event chair, event chair-elect, and liaisons from the City of Littleton, Arapahoe Community College, South Suburban Parks and Recreation, and from city council.