You outdid yourselves for Crosstober 2025 – you joined us for no less than 24 walks, runs, and bike rides that spanned all of San Francisco. Dozens of you explored the Roundabout – our new 38-mile route along the city’s outer edge. Others took part in naturalist-led walks, tours of the city’s famed stairway mosaics, and several mashups that combined our various routes.
An impressive number of you took part in our all-in-one-day Roundabout attempts. Just as impressive are all of you exploring the Roundabout on your own: check out ’roundabout trail sf’ on Instagram.
Thanks for joining us for an entire month of urban adventure! Our event leaders filed these reports:
Crosstown Trails founder Bob Siegel led several outings that introduced walkers to sections of the Roundabout. His co-lead, Lily O’Neill, captured a few group shots.
Bob Siegel (in Crosstown shirt & cap) and Roundabout Section 1 walkers on October 5Bob wrapped up Crosstober on October 29 with a walk on the Roundabout’s Section 4.On October 11, 50+ people joined Sevy Swift for the inaugural Upper Wedge Trail walk, with 13 doing the entire 27 miles. Experience it yourself through Sevy’s delightful Substack article and Instagram video.This mural, tucked into a Glen Park side street, popped up on the Southside Ramble that Chris Rupright, Arnie Thompson, and John Trevithick led on October 22. Walkers explored the city’s southern half on a route that combined the Crosstown Trail, the Double Cross, and the Roundabout. “Even longtime Bay Area walkers were excited to explore neighborhoods and landscapes that were new to them,” says John.Can you bike the Roundabout? On October 25, a small group of cyclists braved misty rain to find that the stretch between Daly City BART and Embarcadero BART is indeed a doable and interesting ride. Riders fueled up at Mission Blue in Visitacion Valley and at the BBQ pop-up at India Basin Waterfront Park. Watch on YouTube: Half Roundabout by BikeOn October 25, dozens of folks zipped up their rain jackets for a 5+ mile walk of San Francisco’s iconic tiled stairways, the grand finale of this year’s SF Stairway Month. Joining hike leader Alex Kenin were special guests Aileen Barr and Colette Crutcher, the mosaic artists behind the walk’s four featured stairways, and Renee Berger, organizer of Stairway Month. The walk ended with a lively neighborhood party at the Burnside Steps in Glen Park. See more on Instagram.Helen Doyle led three Crosstober walks along the Roundabout, co-sponsored by Nature in the City. The October 26 walk featured diversions to explore Mission Creek, the Pier 94 wetland, and the shorebirds of Heron’s Head. “Many people expressed pleasure at seeing parts of the city they’d never been to, and, of course, learning more about the city’s human and natural history,” says Helen. “We also enjoyed several new Big Art Loop installations along the way.”
On October 24, 25, and 26, a rotating cast of explorers joined leaders Nancy Botkin, Guy Joaquin, and Karen Rhodes to walk the entire Roundabout, covering about 13 miles each day. Throughout, we were graced by the presence of walkers who are active with the Bay Area Camino Pilgrims, who infused our journey with joy and presence.
“Truly, this was a circumambulation – walking in a circle around a sacred place,” says Karen. “After all, we were all doing what we love and sharing that with others.” Adds Guy, “Of course, it was a blast to walk the city’s entire edge, but the real joy was the people. Every day felt like the first day of school, wondering who would show up to walk, chat, and share the journey. And I loved hearing ‘Wow, I’ve never been here before’ over and over.”
Day 1: Ferry Building to Visitacion ValleyDay 2: Visitacion Valley to Lands EndDay 3: Lands End to the Ferry Building
See more stories on our Instagram profile, including the October 5 walk on the Roundabout’s Section 3 led by Johanna Lopez Miyaki and Mary Nite.
Thanks to all the Crosstown Trails volunteers who helped make this year’s Crosstober a huge success. What’s next? We’re already thinking about solstice walks, a “Camino de San Francisco,” and other events that celebrate community-building through urban exploration. Be sure to subscribe to our mailing list (see our home page) to get the word. Interested in volunteering? Email us!
