Urban rappelling – a concept I hadn’t even heard of until a few months ago, when a friend invited me to participate in this year’s Outward Bound California City Skyline Challenge: rappelling off of the roof of the Hilton hotel in Union Square, San Francisco. So a few days ago, that’s exactly what I did! Thanks to my generous donors, we contributed over $2,500 toward Outward Bound’s total target of $300,000.

Urban rappelling - on the roof

On the roof of the SF Hilton. (All of the images here were taken by me, using a GoPro strapped to my helmet – courtesy of GoPro, one of the event sponsors.)

The event

The event was managed by Over the Edge, which apparently specializes in urban rappelling fundraisers for non-profits. And what more fitting non-profit than Outward Bound for such an event!

Stepping off the edge.

They had rappellers throughout the day, with two sets of ropes so that two people could be rappelling down at any given time, either together or at their own pace. That meant everyone had a time window: We were supposed to show up at a certain time; get geared up downstairs; head upstairs to enjoy the view from Cityscape (restaurant) on the 46th floor of the Hilton and get an Outward Bound orientation; climb up the last set of stairs to get onto the roof (no, they did not make us climb all 46 floors, we did get to take the elevator) – and enjoy an even more amazing view. You’re not really much higher at that point, of course, but you are out in the open.

The day was sunny, warm, not windy, not foggy and not (thankfully) smoky from the wildfires in the vicinity. Unfortunately, I could not take pictures from there, since we were not allowed to bring anything with us, not even in closed pockets, to avoid the possibility of anything falling down from the roof to the streets below. On the roof, we got our safety talk and a mini practice session, so that everyone knew how to operate the equipment.

There is more to us than we know. If we can be made to see it, perhaps for the rest of our lives we will be unwilling to settle for less.  Kurt Hahn, Outward Bound Founder

Urban rappelling equipment

I’ve rappelled before in wilderness settings but had never tried urban rappelling. What we had yesterday had some additional safety precautions built in – which makes sense, since they had the whole range of people participating, from “I’ve never done anything remotely like this before” to “sure, I’ve rappelled all over the world”. It was reassuring, but not surprising, to see that this was pretty much fail-safe: One handle for releasing tension and allowing you to let yourself down the main rope; if you wanted to go slower, you simply moved it up; if you wanted to go fast – well, you couldn’t really, because quickly it would hit a stop and lock up altogether.  

That also meant that if you panicked and grabbed the handle, you’d most likely yank it all the way down and – immediately set the brake. Very well designed. The second rope we were each on simply had a friction braking mechanism – as soon as you might start to go too fast, as in a fall, it’d simply lock right into place and stop you there. Redundancy everywhere, very safe.


I was also really impressed with the staff’s professionalism. Everything was double and triple checked: for example, my own harness had already been checked three times; when the time came for me to be clipped into the two ropes, one person did the work; then when he

Hello, Cityscape diners!

was finished, a second person came and checked everything that had just been done. I’m guessing their safety track record at these events is flawless. Communications were excellent between top and bottom. Instructions were clear. They gave people the right mix of encouragement and calm.

Looking up to where I've just come from.

Wow, I’ve already come a long ways!

So, what was it actually like to be urban rappelling?

There was a TV reporter from a European channel, who asked me a few questions while I was waiting for a couple of people ahead of me to finish their descent. She asked me if I was nervous, and I said no. But I also admitted that I wasn’t afraid of heights and that I had a lot of faith in the rope system that they had put up. I told her to ask me again while I was actually standing on the edge, about to step off. She didn’t (no one other than staff and current rappellers were allowed right there), but my answer wouldn’t have changed. The whole process was simply very well done and quite clearly very safe. So I could just enjoy the feeling of being up there without anxiety.

Stepping up, walking down

When it was my turn, I walked to the “wall” at the edge and sat up on it, facing in toward the center of the roof/building. For anyone afraid of heights, this was a great design: you at no point had to face forward/outward and look down. In fact, if you hadn’t wanted to, you could have done the whole thing without ever looking down. Instead, I sat on the edge facing back toward the building and waited for them to clip me in and make final adjustments, radio down to say I was ready, and send me off.

Still a long way to go!

To start, I had to stand up on the ledge, grab on to the supporting structure that anchored all the ropes at the top, and then gently “sit down” into thin air. Sounds scary but in reality, you actually had to work a bit to actively feed rope through the equipment, to get started. There’s so much weight of the rope below you that it creates a lot of friction. Without actively feeding rope through, you really aren’t going anywhere, particularly if you’re on the lighter side. So the beginning is extremely gentle.

After that, you simply walk backwards down the wall while keeping the lever at the right amount of tension and feeding rope through. Repeat about a thousand times. It required no particular dexterity or fitness.

I did find the harness kind of uncomfortable on my lower back, which unfortunately made turning around to look out and about mildly painful. And if you had zero fitness level, then the “walking” motion of your legs might get exhausting after a while – there was some “work” involved. Of course, I could always stop to sneak a peek around or up or down or simply reflect on how lucky I was to be up there to enjoy this experience.

Nearing the bottom.

Not only can you stop at any point simply by doing nothing, even letting go with one or both hands simply meant that the device would immediately stop you from descending further. I also did a few small horizontal jumps away from the wall. They were somewhat behind schedule when I went down, so I didn’t hang out for too long, though. I’d hate for someone else to miss out on their chance because of it getting late.

Peace and tranquility @ the 40th floor

I didn’t mind not being able to look backwards too much, because what I found I most enjoyed about the experience was the quiet and feeling of tranquility especially in the top half. This was completely unexpected for me. Once I went over the edge and traveled down a ways, I really couldn’t hear the people on the roof, and I was high enough that the traffic and normal city sounds hardly reached me at all. It wasn’t totally quiet, but enough that it simply felt peaceful up there, dangling from the roof. I could have happily just stopped and done nothing but literally “hang out” for a good long while.

Who knew that dangling from a rope at about the 40th floor of a skyscraper could be so calming and peaceful?

I’m used to peace and quiet and tranquility when backpacking or climbing in the mountains, but I would never have guessed I’d find that in the middle of urban rappelling in San Francisco. That was my single biggest personal takeaway from this event.

Working through fears

urban rappelling

Watching the rappeller next to / after me.

Another thing I thought was amazing to watch on the roof was how different people processed whatever fears they faced in stepping off the edge. Being afraid of heights was not uncommon – and yet a number of people managed to breathe their way through and, with the support of the staff, step off anyway.

One person ahead of me got to the edge, got clipped in, breathed deeply for a few minutes, and got clear that this was not for her – that, too, was impressive: She works for one of the event sponsors; there had to have been a lot of pressure on her to do this – and yet she found the courage to say “no.” Equally great: everyone there supported her in that decision. I have been in other situations where the opposite happened – this was MUCH better.

The time to be still is past. It is time to go. Do something that matters. And never look back. Outward Bound

All in all, a great event – I’m already thinking of doing it again. Outward Bound California City Skyline Challenge 2020? Who knows, maybe urban rappelling can become a new hobby. (No, I do not need another hobby!)