The land on which the Valley of the Moon Winery and Vineyards is located has an illustrious past. Once, it was part of the vast 48,000-acre Agua Caliente Land Grant owned by General Mariano Vallejo. Subsequently it changed owners several times until 1863 when the "Stone Tract" portion of the property was conveyed to Mr. George Whitman. According to the best records, Mr. Whitman was the first owner to grow wine grapes on the land. He built a winery and by 1876 his enterprise was a successful one, annually producing 50,000 gallons of wine and 2,000 gallons of brandy.

In 1881, Whitman granted a portion of his property to the Sonoma & Santa Rosa Railroad Company. A passenger train station was built and tracks from Sonoma to Glen Ellen were laid down. Two years later, Whitman sold the property to Mr. Eli T. Sheppard, former consul to China, and later an advisor in international law to the emperor of Japan. Sheppard named the property "Madrone Vineyards" and in 1887 began constructing the first of two stone wine cellars on it. Due to poor health, Sheppard retired to San Francisco the following year, and sold the vineyards and winery to Senator George Hearst, father of newspaper magnate William Randolph Hearst. Senator Hearst lived on the property, further developing Madrone Vineyards into a serious winemaking operation. He proudly served his wine to guests in Washington, D.C. In 1891 Hearst died, leaving the property to his widow.

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