Our new Roundabout is our most audacious trail yet – 38 miles around the perimeter of San Francisco. Starting and ending at the Ferry Building, the route follows the city’s outer edge, along the San Francisco Bay, the Daly City border, the Pacific Ocean, and the Golden Gate strait. You can cover the Roundabout a section or two at a time, or even in a single day (!). The six sections range from five to eight miles in length and cover a variety of terrain.
As you explore the Roundabout, you’ll see all that can unfold where land meets water. Fort Funston, Sunset Dunes, and the Presidio are rich in scenic views and coastal habitats. The city’s northern waterfront, from Crissy Field to the Ferry Building, includes a wealth of public promenades and iconic port architecture. And the southern waterfront – quickly becoming a necklace of connected bayside parks – will show you glimpses of the city’s maritime and industrial history.
You’ll also meander through the city’s southernmost neighborhoods. Visitacion Valley, Crocker Amazon, and OMI (Ocean View, Merced Heights, Ingleside) offer delightful discoveries for even seasoned San Franciscans. Generations of families have made their homes here and created a strong sense of community, with locally owned businesses, pocket parks, and public art.
What inspired us to create the Roundabout? We got acquainted with a group of folks who, twice a year, walk the entire perimeter of the city in one day. You won’t find them on a website or social media – all you need to do is to show up at the Ferry Building at 8 a.m. on the first Saturday of the spring or fall. You can read Tina Martin’s account of her own 32-mile perimeter walk on Senior Beat: The Biggest, Best Walk — and Bath of a Lifetime.
Yes, our 38-mile Roundabout is a bit longer. When we design crosstown routes, we can’t resist including expanses of parks and open space, sites of historical and cultural interest, a moment or two of whimsy, and other features that make San Francisco such a compelling destination for exploration and outdoor adventure.
As Crosstown Trails founder Bob Siegel told the San Francisco Chronicle, “This is going to blow people’s minds out there. We wanted to showcase another side of the city. We wanted to connect the neighborhoods. We wanted to show that there are a lot of trails you may not know about.”
In a way, another inspiration for the Roundabout is the spiritual tradition of circumambulation: the ritual act of walking around a sacred place. Your Crosstown Trails volunteers love this city with a passion and take joy in providing you with new ways to explore its treasures.
Read Peter Hartlaub’s account of his Roundabout adventure here.
You can find maps, turn-by-turn directions, and more information under our Roundabout tab.