In Sycamore Grove Park, Dos Mesas Winery is a place few people know about. A place steeped in history that has housed many different tenants over the 125 years of its existence.

The story begins with Dolores Mesa and his son, Ysidrio, who originally owned the land, which is now part of Sycamore Grove Park. This father and son ranched the land and called it "Dos Mesas," referring to their family name. 

In 1883, Douglas and Frank Fowler purchased the land and began growing grapes, eventually extending to 56 acres. At the time, this was known as "Fowler's High-Type Vineyard," it was famous for its red Bordeaux blends. Eventually, in 1895, the land was sold to a German-born man named Theodore Grier. Theodore worked tirelessly and had 225 acres of vineyard in the Livermore Valley by the turn of the century. Grier is credited with being the first person to plant Chardonnay grapes in the valley. By 1907, Grier's 225 acres grew to around 1,000 acres (about half the area of the Philadelphia Airport), and that was solely made up of the vineyard rows. While Grier was an incredibly successful vintner, he was also very outspoken with disputed personal views throughout his lifetime. 

Eventually, in 1899, Theodore Grier sold the Dos Mesas property to Dr. L.E. Cross, a physician, businessman, and aspiring vintner. Dr. L.E. Cross had a brother, Dr. Harry Cross, who was in poor health, which led him to give up his practice and start a new winery.

The Cross brothers built this additional expanding complex, which by 1902 had included the main building, a bottling plant, a cooperage, 125 acres of vineyards, and a wine cave. The main building is two stories tall, with the first floor made of cement while the second floor was used for fermenting the grapes. The first floor was utilized as a work area and wine storage. This location allowed for gravity to be used in processing the wine, although it is noted that a modern gasoline engine was also used to transport items between floors. The wine cave was located next to the main building and was tunneled 150 feet into the hillside. It contains two spurs, one being 50 feet with the other at 75 feet. There was also a small set of tracks that allowed carts to travel from the cave to the bottling building.

The Cross brothers retained the name of Dos Mesas for their new enterprise, and despite being hopeful of becoming successful vintners, this aspiration had unfortunately shortly diminished. During the great earthquake of 1906, the brothers' extensive holdings in San Francisco were utterly wiped out along with the city, leaving them bankrupt. 

In 1907, the land was acquired and renamed Cresta Blanca number two, given by the Wetmore/Bowen company owners of the Cresta Blanca winery. These winery owners were well known for their fine Sauternes on site, but they used the old Dos Mesas facility for their sparkling wines. Several years later, in 1923, Dos Mesas was purchased by the Veterans Administration as a site for the new hospital. The wine industry, along with Cresta Blanca winery in particular, was reeling under the effects of the prohibition, forcing them to liquidate all of their collective holdings. Eventually, the Veterans Administration acquired the land, later building another residence to house the nurses who worked at the hospital. 

In 1967, the Livermore Area Recreation and Park District purchased 32 acres of the Dos Mesas property from the federal government. This began to form what is now part of Sycamore Grove Park, officially becoming established a few years later in 1974. The old winery still sits at the park today, forgotten and full of history.