Then and Now: Flying Y Ranch and the Dipsea

When the 101st edition of the Dipsea Race was held earlier this month, hundreds of people gathered at the start and finish lines and all along the course to get a look at the legendary 7.5-mile footrace. 

Most of the Dipsea trail traverses over public parks or government land, including open space, Mt. Tamalpais State Park, Muir Woods, as well as the towns of Stinson Beach and Mill Valley.

When the race started back in 1905, there were very few people living in Mill Valley, and even fewer along the trail once the runners left downtown. In those early days, the Dipsea trail was called the Lone Tree Trail and most of it was on privately owned land. William Kent was still a large land owner for much of what covers Muir Woods and the Steep Ravine area. Read Barry Spitz's book, Dipsea: The Greatest Race, for a marvelous account of the development of the Dipsea trail and race.

This week's Then & Now focuses on just one of the areas of the Dispea race course that was privately owned for many years. It was and still is known to runners as the Flying Y Ranch. The ranch is located on what is now called Walsh Drive. It is just one-quarter of a mile past the top of the final flight of stairs. Currently runners run up Walsh Drive, which is paved. At the top, they enter a dirt trail that has a small resemblance to the dirt path that was there for the better part of 75 years.

From the first Dipsea Race in 1905 to the late 19070s, runners would pass through the middle of Flying Y Ranch. As far as anyone remembers, there was never an issue of the race being run through any of the privately owned lands. Land owners never really thought of much reason to object. Contrasts that today with the constant battles the race committee has with the government jurisdictions that own the public lands, that require permits… it’s a constant headache dealing with those bureaucracies and their agendas.

Originally this land was part of the Throckmorton Ranch, which was a great hunting ground for deer and bear 150 years ago. By the time Mill Valley was formed, it was sold off as “Ranch 5” on the Tamalpais Land and Water company’s map. It split off in 1910 within the Marin View acres sub division and became a dairy ranch, known as the Flying Y Ranch. 

In the 1950s, the ranch became an 11-acre horse boarding ranch. It remained as such until the late 1970s and early 80s, when it was developed by Mr. Walsh. Today, Walsh Drive has fewer than a dozen very large homes with spectacular views of the bay. Although it is called Walsh Drive on the maps, and the street sign says Walsh Drive, runners still refer to it as Flying Y Ranch. 

If you look closely behind an overgrown bush at the base of the hill, there is a large sign that says, “Flying Y Ranch."