February 21st, 2026
17 miles, 2,300 vertical feet, 6 hours
For someone who grew up in the Bay, I certainly felt like I hadn’t seen as much of San Francisco as I should have. I would argue that one of the best ways to remedy this is to walk diagonally across the entire city over the course of 17 miles. This version of the Crosstown Trail starts at Candlestick Park in the Southeast corner of the city and meanders its way through hidden trails, public parks, shopping corridors, tiled stairways, and community gardens to the Lands End Lookout in the Northwest corner of the city. After completing this, I would highly recommend it to anyone looking for a change of pace from backcountry hiking or trail running, or just to get a new perspective on San Francisco.
Ross and I met up at Candlestick Point at 9 am and headed as far Southeast as we could to begin the hike. From there, we hugged the water on a rapidly eroding trail until meeting up with some pavement to cross under Highway 101 and walk through Little Hollywood into the Visitacion Valley Greenway.
The Visitacion Valley Greenway was so cool! After a brief block and a half of walking on the sidewalk, we headed up the hill in a green corridor surrounded by community gardens and murals. Topping out in a neighborhood before entering McLaren Park, we had an incredible view of the Bay and San Bruno Mountain.
Walking North through McLaren Park, Ross and I crossed over Highway 280 and through Saint Mary’s Park before meeting Pegels and Dylan outside of the Glen Park BART Station about six miles in. The beauty of this route really is its accessibility. The abundance of public transit along the way easily allows for section hiking and for folks to join or leave as needed along the way. I had planned out a robust timeline that allowed us all to plan meeting points and times throughout the day, and it turned out to be pretty accurate!
As a group of four, we walked through Glen Park and made our way up through Glen Canyon Park. We got some extra vert climbing up to a rocky viewpoint, and then circled Sutro tower as we circumnavigated the Laguna Honda Hospital, finding historic looking caches of old glass bottles alongside their contemporary counterparts.
After dropping down to the Forest Hill Station and climbing back up to Golden Gate Heights Park, we met up with Lexi, Ivan, and Daytona at mile 10. Together, we cruised down from the high point of the trail and ditched Ross on Judah Street. At this point the trail took on a more urban vibe than the first half as we stuck to continuous pavement. After stopping for water, we met up with Ty and entered Golden Gate Park.
In Golden Gate Park, we walked around the West side of Blue Heron Lake and Strawberry Hill, passed the log cabin, and walked through the (seasonally sparse) rose gardens. As we followed Highway One North for a mile, we were able to stick to a nice parallel trail, although crossing each road was still a pain. After reaching the Presidio, we turned to the West and started making our way along the boardwalks to the beach.
With everyone’s legs anticipating the end (including my own), we turned off the beach and walked through the Sea Cliff neighborhood. Some of the views of the Marin Headlands, even from the sidewalk through some of the nicest houses I’ve ever seen, were beautiful enough to take my breath away. With some of the displays of wealth at hand, I was pleasantly surprised to even be able to walk through the area without getting hassled by gated access or private security.
We crushed the last two miles from Lands End to the Sutro Baths and called the trail a success! After an elapsed time of 6 hours, looking at the map of the trail that we had just accomplished was so cool!
We stopped for tacos and then parted ways. On my drive back to Monterey, it was surreal to see snow on some local South Bay peaks. I definitely plan to head back up for both the Double Cross Trail (15 miles Southwest to Northeast) and the Roundabout Trail (38 miles clockwise from the Ferry Building), but for now I feel satisfied walking away with a little more time on feet, and a better understanding of San Francisco.
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