Chief among those moving early onto the mountain to establish vineyards were Jean Adolph Brun and Jean V. Chaix—two experienced vintners who planted hundreds of acres of vineyards and made a success selling the wine they produced. Because they also owned an Oakville operation (today the location of The Napa Wine Co.), they were among the most successful local wine businesses during the boom of the 1880s. Eventually the operation sold out to others and was closed during Prohibition. Since then, however, it has been completely renovated, and is now home to Ladera Vineyards.

Other famous winegrowers who moved to the area were Charles Krug, W.A.C. Smith, Frederick Hess, and W.S. Keyes who started Liparita Vineyards and then built another stone winery, known as La Jota today. By the end of the decade, there were more than 600 acres of wine grapes planted, and the vineyards on Howell Mountain had developed an excellent reputation for their wines.

In 1889, the Howell Mountain region made history when Brun & Chaix won a Bronze metal at the Paris World Competition. Ten years later, Keyes took gold and bronze, while Hess walked away with bronze for his La Jota Vineyard Co. Blanco table wine. Later, in 1904 at the St. Louis Exposition, Keyes repeated his Paris triumph by winning the grand prize for his renowned red wine. Collectively, these medals proved the longstanding reputation of Howell Mountain wines.