The San Francisco Bay Area, despite its massive population, holds an equally massive amount of protected land: networks of multi-use trails and campgrounds stitched throughout. You trade remoteness for convenience, but this kind of variety is something I love to fold into my bikepacking goals. Plentiful food, quality sleep, hard-charging downhills—elements worth remembering the next time you’re really out there and feeling a bit thrashed. My introduction to the area was the SF Peninsula Traverse, a route I used to start a weeklong ride from San Francisco Airport to Los Angeles Airport in 2019. In 2024, Adam Sklar showed me around some of the Marin and Fairfax classics. I’ve been fascinated by the sheer number of options ever since, to the point that my Gaia GPS maps are now borderline too cluttered to navigate. Looking for ways to combine the SF Peninsula Traverse with the Bay Area Triple Crossover led us to Bikepack the Bay—a 265-mile, +27,000ft route that we trimmed slightly to fit more comfortably into a three-day window with limited December daylight. Day 1 covered 64 miles and +5,600ft from Sklar’s shop in the Mission District, following the SF Peninsula Traverse through Half Moon Bay, climbing into the redwoods (at night), and dropping into a Palo Alto hotel. The route starts urban, slowly dissolving into crumbling abandoned roads through the hills, coastline bike paths, and finally a lush, pine-needle climb that’s absolutely grueling. From Skyline Road, the Kings Mountain Road descent—ridden in the dark—was the best road descent of my life. Dynamo-illuminated reflectors twisted through the redwoods like the ultimate video game. Day 2 began with a long bridge and shoreline crossing, then followed nearly the entire skyline from Fremont to Richmond along the Bay Area Ridge Trail (decently signed). 77 miles and +7,700ft. Spending the entire day on bike paths, wide dirt roads, and ripping singletrack was hard to believe given the proximity to millions of people. Fifty-two-tooth cassettes and the absence of camping gear were especially welcome for just how steep every climb was on this stretch. Day 3 opened with another bridge traverse and 67 miles of +7,300ft along ridge top fire roads to Lagunitas—the only resupply point—before a final push along Bolinas Ridge, around Tam, and across the Golden Gate back into San Francisco. Once again, a full day without really touching a road. We skipped the Headlands trails as sunset approached, but there are plenty of options to explore there. The varied, ever-changing terrain kept us engaged. The urban offered a reprieve from the steeps; the steeps, a reprieve from the urban. Staying in cheap hotels felt like a luxury—less luggage, more riding. Kyle is typically the route master when we’re out together, but I believe I showed him some things to change his perspectives this time around. The Bay Area is about to be one of our winter classics. Tips– Navigation is constant. A head unit is essential, and having the tracks on your phone as backup is smart. Trail closures around the Baylands in Palo Alto before the bridge crossing added a few miles of backtracking– The Richmond Bridge closes the bike lane during the week but offers a free shuttle bus in its place. If you want to ride it, check schedules and plan a weekend crossing– Keeping a variety of Bay Area routes saved allows for easy on-the-fly modifications or side quests– SFO Airport offers luggage storage and a bike stand if you want to start and finish the loop there Incredible resources:SF Peninsula Traverse – https://bikepacking.com/routes/sf-peninsula-traverse/Bay Area Triple Crossover – https://bikepacking.com/routes/bay-area-triple-crossover/Bay Area Ridge Trail – https://ridgetrail.org/Bikepack the Bay – https://www.bikepackthebay.com/ --- Thomas Woodson is a Colorado-based photographer and Moots ambassador known for capturing long days, quiet moments, and the kind of riding that rewards curiosity over convenience. He currently rides a dropbar MXC in our Groundswell finish, a setup well suited to the mixed terrain and exploratory routes that shape his work.
