Downtown Pleasanton is a historic district of business and residential properties located in a relatively small geographic area in the southeast corner of the City of Pleasanton. In the year 2000, Pleasanton joined the ranks of certified California Main Street Communities, a designation bestowed by the state's Trade and Commerce Agency under the auspices of the National Main Street Center. This esteemed recognition is a symbol of the community's history and unity.

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To walk through downtown Pleasanton is to take a walk back in time, past historic old buildings, many once connected by secret tunnels under Main Street. Each building has its own story to tell. Some tell stories about Mary Pickford, Phoebe Apperson Hearst, Abbot & Costello, Presidents, and the famous racehorse Seabiscuit. Others speak of lawless bandits like "Three Fingers" Jack Garcia, bank robbers that got away, a speakeasy shut down by Earl Warren, a brothel or two, and a Prohibition-era racketeer named Paul "Bouquet" Cohn.

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A few may even have ghosts from their pasts. These beautiful buildings display a variety of historic architectural styles, from Victorian, Italianate, Richardson Romanesque, Mission Revival, and Colonial Revival to Craftsman, Art Deco, and Moderne.