Less than 300 years ago, San Francisco was a land of hills and sand dunes, where Ramaytush-speaking Ohlone lived in seasonal communities along creeks and the Bay. They lived lightly on the land in sharp contrast to the dense urban city we know today.
San Francisco’s Double Cross Trail invites us to imagine that not-so-distant past and envision a future more deeply connected with the natural landscape. Added as a companion to the original Crosstown Trail in June 2024, the 15-mile Double Cross diagonally traverses the city from its southwest corner at Fort Funston to the northeast at the Embarcadero, passing by freshwater lakes and former creeks that once flowed to the Bay, climbing hills and stairways to jaw-dropping views, and winding through historic town squares where native plants and wildlife still thrive.
While many hikers challenge themselves to do this trail (and the Crosstown) in one day, the route can also be divided into two or three sections, with end points reasonably accessible via public transit.
Fort Funston to West Portal: Water, Fog, and Dunes
The trail begins at Fort Funston, on the city’s southwestern shore, where a California sea lion playing in the waves below the foggy bluffs sent us off. An osprey soared over Monterey cypress trees sculpted by near-constant wind. As in many coastal areas of California, the invasive South African ice plant dominates the dunes. Farther north, however, native coastal and Chamisso bush lupines, coast paintbrush, and seaside buckwheat thrive in the sandy soil and moist air. On the landward side, sticky monkey flower, coyote brush, and California bee plant find their place.
In contrast, the shoreline of nearby Lake Merced is a tangle of water-loving plants like California bulrush, arroyo willow, and red elderberry, alongside trailing blackberry and common ivy. From spring through autumn, Pacific forktail damselflies mate amid colorful wildflowers—tidy tips, Menzies’ baby blue eyes, and California poppies.
Lake Merced is a natural freshwater lake draining the high points of western San Francisco and Daly City. Human activities—golfing, boating, a police shooting range—have dramatically changed its shoreline, and urban runoff has contributed to degrading its water quality. But songbirds and flycatchers still find food and refuge in the trees and shrubs, and introduced fish forage among the willows and bulrushes. Also called tule, these hollow reed-like plants were used by California’s Indigenous people to make baskets and boats. The Annals of San Francisco, published in 1855, reveals that Lake Merced once breached a sandbank and emptied into the Pacific Ocean, possibly due to heavy rain.
Fed by the same aquifer as Lake Merced, Pine Lake sits at the west end of Stern Grove but is largely hidden from the thousands who attend the Grove’s free summer concerts. In a valley surrounded by steep, forested slopes, the lake supports many native plants, like arroyo willow, California bulrush, California buckeye, coast live oak, toyon, and California manroot.
In a city as densely built as San Francisco, with most natural waterways buried or rerouted, these few remaining natural lakes provide vital wildlife habitat, including for birds migrating on the Pacific Flyway.
West Portal to Duboce Park: Up and Over the Hills
This middle section of the Double Cross features parks like Twin Peaks, Tank Hill, and Buena Vista Park. These steep, rocky hills, geologically part of the Franciscan Complex of the Marin Headlands, slowed development of the city’s west side until two streetcar tunnels were built in the early 1900s: the Twin Peaks Tunnel from the Castro to West Portal and the Sunset Tunnel from Duboce Park to Cole Valley. While today’s trains can make it through the tunnels in minutes, hiking this five-mile, up-and-down section from West Portal to Duboce Park deserves a few hours at least.
These hilly landscapes retain some of the last remnants of San Francisco’s native coastal scrub and grassland habitat. The San Francisco Recreation and Parks Department manages them as “natural areas”—prioritizing their biodiversity and “wildness” over recreation and facilities. On Edgehill Mountain, eucalyptus and Monterey cypress shade and crowd out the native landscape. But the recent thinning of trees below the trail will allow existing native shrubs—red elderberry, flowering currant, California lilac—and trees like coast live oaks to thrive, restoring this steep hillside to its more diverse habitat. Like many of San Francisco’s hills, Edgehill Mountain was quarried for rock to build the city and requires massive structures to prevent slides.
The next hills are the Twin Peaks: Noe and Eureka. At Portola Drive and Twin Peaks Boulevard, the Crosstown, the Double Cross, and the Bay Area Ridge Trail intersect—a point dubbed the Tri-Trail Junction by the San Francisco Crosstown Trails Coalition. From Portola the trail climbs through a cacophony of ornamental plants, such as the showy Pride of Madeira. At the top of Twin Peaks, silver bush lupine, seaside buckwheat, and other natives serve as essential habitat for the Mission blue butterfly. Christmas Tree Point gives the first views of densely built downtown San Francisco.
Below Twin Peaks, several smaller rocky peaks also reveal the city’s natural and human history: Tank Hill, where the Spring Valley Water Company operated the Clarendon Heights Water Tank, built in 1894 and removed in 1957; Mount Olympus, where the lit-up “Triumph of Light” statue, erected by Adolph Sutro in 1887, allegedly confused sailors who mistook it for a lighthouse; and Buena Vista Park, one of the city’s oldest parks. From here the Double Cross drops down to Duboce Park, passing through the shady woodland habitat of Adah’s Stairway—named in honor of Adah Bakalinsky, author of the well-loved Stairway Walks in San Francisco. (She passed away in late 2024 at the age of 101.)
Duboce Park to Pier 23: Iconic Views and Public Spaces
The final section of the Double Cross stretches across historic neighborhoods—Western Addition, the Tenderloin, and Chinatown—where the narrow sidewalks and busy streets leave little space for greenery. And what nature remains is not natural, since the landscapes were heavily changed in the decades following the Gold Rush.
But this section also delights with picture-worthy views and colorful history. Alamo Square, dedicated in 1856 by Mayor James Van Ness, is said to have gotten its name from a cottonwood tree that stood here when it was a stop on a horse trail (álamo is the Spanish word for cottonwood or poplar). The park now sports a variety of native plants as well as Monterey cypress and grassy lawns for lounging. Like Nob Hill’s Huntington Park and North Beach’s Washington Square farther along the trail, this urban haven is excellent for people-watching and city views.
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And you can still find nature in this urban landscape: Patricia’s Green in Hayes Valley has replaced the Central Freeway, large planters in front of City Hall tell the story of historic creeks, and mature trees along streets in the Western Addition offer shade and refuge for birds and insects. Telegraph Hill—originally a treeless, rocky outcrop—now supports a mix of native and nonnative plants (as well as the iconic Coit Tower). The two stairways on its eastern side, extensions of Filbert and Greenwich Streets, take walkers through lush gardens, dotted with hidden benches and art pieces. These tucked-away public gardens have been maintained by dedicated neighbors over the generations. Telegraph Hill is also home to the famous wild parrots of San Francisco (actually cherry-headed conures native to Ecuador and Peru), which became the city’s official animal in 2023.
The trail ends on the Embarcadero, where the bay supports a diversity of marine life, including a pair of sleek harbor seals that greeted us on our arrival. With all the fill and concrete bordering the shoreline, it’s easy to forget that San Francisco Bay—one of the largest estuaries in the country—is a vibrant ecosystem. Like the Pacific Ocean, the Bay has enormous influence on the city’s climate, natural habitat, and human history, from the days of the first Ohlone tribes to today.
The Double Cross Trail, like the original Crosstown Trail, invites urban explorers to let their minds wander through these histories as their feet carry them across San Francisco.
IF YOU GO
Double Cross Trail
The draw: Urban hike with views of the Bay and Pacific Ocean, natural lakes, hills, and public parks.
Trails: 15 miles, including staircases, trails, and paved streets.
Getting there: Fort Funston Road, San Francisco 94132
Facilities: The Fort Funston parking lot has pit toilets. Public restrooms are also available at Lake Merced Park, Alamo Square Park, and other points along the 15-mile trail.
Online: Find turn-by-turn directions and maps at CrosstownTrail.org.
