June offers 15 guided walks on the Crosstown, Double Cross, & Roundabout!
As June rolls in and daylight stretches well past dinnertime, it’s officially peak season for longer walks in San Francisco.
Luckily, the amazing volunteers behind the Crosstown Trails have given us not one, not two, but three epic routes to explore San Francisco: the original Crosstown, a 19-mile route linking the southeast and northwest corners; the Double Cross, a 14-mile route connecting the southwest and northeast; and The Roundabout, introduced last year, an epic 38-mile loop around the perimeter of the city.
If you’re getting blisters just by thinking of it, don’t be daunted by the mileage. These routes are designed to be tackled in segments, and the Crosstown website shows you how to break them into manageable adventure bites.
And this June, you can experience parts – or all – of these routes alongside fellow urban walking enthusiasts during the Crosstown’s 7-Year Anniversary celebration. With 15 events on the calendar, there’s something for everyone, whether you’re a seasoned urban explorer or just getting started discovering San Francisco on foot.
A few friendly Walk SF faces will be leading walks, too. I’ll be on the Crosstown Triple Play on Monday, June 15 and the Crosstown Zigzag on Thursday, June 17, two meandering mashups of all three routes.
On the weekend of June 6, Walk SF Board member Karen Rhodes will lead the full Crosstown over two days, and then the full Double Cross also over two days the following weekend, June 13 and 14.
Are you ready for the whole enchilada? I’m teaming up with Walk SF members Harrison Anderson and Eric Chase (also longtime member of WalkLab, the volunteer crew behind all of Walk SF’s walks, like Peak2Peak and the SF Stair Challenge) for a full dawn-to-dark push on the entire 38-mile Roundabout – all in one day on Saturday, June 27. Crazy? Maybe. Unforgettable? Definitely!
No matter if you join for a few miles or the full route, these events are a reminder of what makes walking in San Francisco so special: secret gardens and pathways, pockets of nature, outdoor art, sweeping views, hidden stairways, and the simple joy of seeing the city at human speed. So lace up your shoes, pack some snacks, and come celebrate seven years of Crosstown adventures with us. Are you in?
