There are few things I love more than conjuring up an entirely arbitrary challenge. Oh – except San Francisco. And climbing hills. And stopping to take photos. So, obviously, the moment I came across this “Real Top 10 List of San Francisco’s Steepest Streets,” I had to map out a route to run them all in one go.

I transcribed this quote from Maya Angelou in my notebook last year, thinking to myself that it was the perfect way to phrase why I will never be a person who runs the same route every day: “Because of the routines we follow, we often forget that life is an ongoing adventure… and the sooner we realize that, the quicker we will be able to treat life as art…”

On days when I’m depressed, or overwhelmed by a sense of purposelessness, sometimes the best thing I can do for myself is make up a “silly little project”; something that simultaneously gives me a sense of accomplishment but also reminds me that life is something I can choose to approach with an attitude of curiosity and adventure. And, of course, an excuse to do something other than doom scroll and ruminate over my shortcomings and anxieties.

San Francisco’s steepest streets, according to the list above, are as follows:

1. Bradford above Tompkins (41% grade)
2. Romolo between Vallejo and Fresno (37.5% grade)
3. Prentiss between Chapman and Powhattan (37% grade)
4. Nevada above Chapman (35% grade)
5. Baden above Mangels (34% grade)
6. Ripley between Peralta and Alabama (31.5% grade)
7. 24th between De Haro and Rhode Island (31.5% grade)
8. Filbert between Hyde and Leavenworth (31.5% grade)
9. 22nd between Vicksburg and Church (31.5% grade)
10. Broadway above Taylor (31% grade)

I plotted each of the streets on Google Maps:

The neighborhood concentrations (largely around Bernal Heights in the south and North Beach in the north) lent themselves pretty well to an accomplishable point-to-point route. I planned out what I thought would be the shortest point-to-point route, somewhere in the vicinity of 13-14 miles and 2k ft of total elevation gain. Wonderfully enough, I happen to live close by to the first street on the route – 22nd between Church and Vicksburg – so the short distance between my house and 22nd served as a perfect little “warm up.”

From there I hit, in order:

22nd between Church and Vicksburg (31.5% grade)
A short little bop from our house in the Mission. A spot I’ve frequented before, but I never get tired of my “backyard” hills.

Baden above Mangels (34% grade)
Love a good little jaunt in Glen Park, one of the most underrated SF neighborhoods in my humble opinion. Bonus: this one ends in a dead end for cars – but not for those on foot! – at beautiful Dorothy Erskine park. Hypothetically beautiful views of the city as well, but those were not to be had for me on this drizzly day.

Bradford above Tompkins (41% grade)
As someone who has proudly explored much of the city by bike and foot, I can confidently say this was a corner I’d never been to (which makes total sense considering it’s a dead end on multiple sides and surrounded by highways). And much to Maddy’s delight: more hidden stairways she has never climbed!

Prentiss between Chapman and Powhattan (37% grade), followed by the neighboring Nevada above Chapman (35% grade), and Ripley between Peralta and Alabama (31.5% grade)
Ah: sweet, sweet Bernal Heights. When I lived in Potrero Hill I’d run to Bernal Heights Park often, but that meant I’d usually approach it from the north. It was fun to explore the south side of the park – and also an area that’s so generally steep that I’d never end up there on my bike.

24th between De Haro and Rhode Island (31.5% grade)
An anti-climactic ascent as I have run many more Potrero hills than I’d like to admit, but it was fun to reminisce about when we lived there. Another bonus park at the end of this fun cobblestone climb: Starr King Open Space Preserve (home to beautiful poppies in the springtime!).

From there it was a bit of a slog to get the few miles between Potrero Hill and the remaining three hills in North Beach; I’d venture to say SOMA and Market St aren’t the most scenic running areas. This veeerrrryyy flat stretch was broken up by lots of holiday sightseeing, including at the Powell & Hyde cable car stop just off Market St.

Romolo between Vallejo and Fresno (37.5% grade)
Hidden alleys of North Beach! It was tempting to stop at City Lights while in the neighborhood, but then I remembered I still had a few hills to climb and I’m physically incapable of going to City Lights and not purchasing a book. Also tempting to stop for a dumpling as I passed through Chinatown; decided against eating pork buns mid-run for obvious gastrointestinal reasons.

Broadway above Taylor (31% grade)
Been there, done that. (As in: these steep hills are close enough to my office that in moments of utter frustration I have taken to sprinting them at some point or another. Or after I lose a squash match at the nearby Bay Club.)

Filbert between Hyde and Leavenworth (31.5% grade)
Last but not least! I’ve also run this street before, and knew it was close enough to Swensen’s that I’d planned to get a post-run ice cream sundae. To my UTTERY DISMAY Swensen’s was closed for the holidays, and I had to opt instead for some overpriced treats from the new Bi-Rite on Polk.

I made only two wrong turns in the course of this adventure which I’d say is pretty impressive considering quite a few of the streets are incredibly hard to find amidst dead ends, hidden corners, and small alleyways.

I took a photo at each street location … and a gratuitous selfie by the tourist-slammed holiday-themed cable cars at Powell & Hyde:

Other random thoughts I had during the course of this run:

• This is exactly the sort of thing someone would film for TikTok. I should film this, mile by mile, for TikTok! And then I can become a full-time influencer and quit my job and do this instead! No – actually I definitely shouldn’t, because that sounds incredibly arduous and doing so would sap the joy and not-online-ness out of this adventure entirely … and the only point of these stupid challenges is to do them for the joy of it.
• If there were ever proof that I’ve been diligent about doing the mundane PT exercises for my hips and back, it would be the ability to run this route without hip, back, or knee pain!
• That T.S. Eliot quote about “not ceasing from exploration” keeps coming to mind … will need to look it up after my run …
  [post-run Google:] “We shall not cease from exploration, and the end of all our exploring will be to arrive where we started and know the place for the first time.”
• I have to run/hike up all the streets on this list; climbing up the sidewalk stairways doesn’t count on principle because this is the “SF steepest streets” challenge and not the “SF stairways” challenge. I don’t make the rules. Except – wait, yes – I do.

I would wrap up this post by linking to my Strava route, but I don’t want anyone to get the idea they should try to follow it (given the handful of wrong turns and route inefficiencies :D). So here’s a screenshot of the run, including a “gradient map” view for funsies: