Until you actually start hiking, you might think the hardest thing about the Dipsea Trail is finding out where it starts. Your journey on the Dipsea doesn’t start in a mossy wood or a windswept meadow- it starts in a pretty sedate-looking residential neighborhood. Once you find the trailhead, you are on your way to experiencing some of the most astounding views the Bay Area has to offer, a tour through diverse landscapes, and a pretty phenomenal ass kicking. 
   The ass kicking starts very shortly after you find that long-sought trailhead. The Dipsea starts with 3 flights of stairs, comprising over 600 steps. And those flights are consecutive, so as soon as you are done huffing and puffing up one, there’s another one just waiting for you! But the truly maniacal feature about these stairways is that they are paved with well-intentioned plaques that say things like, “it’s not about the destination, it’s the journey!” and “just keep going!” and “Don’t stop now!” and I just want to punch all those plaques in the face. Of course, there are many that are memorializing people who have died, and I know I’m a horrible person for not appreciating that fact but oh my God, so many steps!
   Also, some idiots run this thing. The Dipsea Trail is also the route for one of the oldest foot races in the US. A local legend named Jack Kirk (AKA the Dipsea Demon) ran the race, stairs and all, 67 times. That is, in all likelihood, probably 66 more times than I will complete the Dipsea walking. The Sunset Magazine invites, “all are welcome to hike, run, or hobble up the 688 steps at any time.” I definitely did the latter of those three. 
   The steps are kind of like a bouncer, and once you get to the top you’re in. The residential neighborhood fades away and you are in the woods. It’s awesome. Redwoods tower over you, breaking away to some truly stunning views of the San Francisco Bay.