The San Francisco Roundabout Trail - A urban hike fueled by determination, grit, and pain meds

On October 5, 2025, five of us met before dawn at the corner of John Muir Drive and Sklyine Boulevard. Our goal: Complete the new 38-mile Roundabout Trail. To walk the route in one day, we’d have to keep our bodies moving for over half a day with minimal stops, witnessing the sunrise, the full day, and the sunset. I’d walked up to 34 miles in a day on the NYC Shorewalkers Great Saunter, but 38-miles was terra incognita for me. Internalizing my learnings from the Great Saunter, I popped some “vitamin I” — or ibuprofen before we even started walking.

 Stats: 

• Distance: 41.67 miles — 3 miles longer than predicted. Every extra step hurt.
• Steps: 81k steps — and I felt every single step beyond 60k.
• Time: 14 hours on the dot (6:30 am - 8:30 pm including all stops).
• Company: Started with 5, picked up 4 en route, and ended with 4

 

The Roundabout Trail is broken into five sections, and we decided to start somewhere in the middle of section 4 with the goal of watching the sunset toward the end of the day at Lands End. The morning was foggy as we headed out along Lake Merced and through the Broderick-Terry Duel Site. On the section between Daly City BART and Visitacion Valley, I encountered some more familiar territory. This was a section I had tested for the Crosstown Trail Coalition before the trail launched. 

On this stretch, I enjoyed walking through a less-traveled part of McLaren Park and stopping at Mission Blue for a ginger scallion scone. We also picked up two friends at the cafe. My body was feeling limber, and the anticipatory energy kept the mood positive. 

 

 

At Candlestick Point, somewhere around mile 12, I felt my hips tightening, so my friend Debbie and I skipped the out-and-back jaunt to the fishing pier to stretch.

Past Candlestick, we ventured through Hunters Point. While some of this area was familiar (as I had recently gone to Archimedes Banya for a birthday celebration), other parts, like a stroll through a Recology plant were less familiar. Here, some sections of the trail were closed off and under renovation. Brett, my partner, navigated us through these areas as we ran into a daytime rave and a stray chicken in Bayview.

 

 

By this point (mile 18?), my hips were really throbbing (and not in a good way), so I took two Aleve. I am pretty sure you’re not supposed to take this much Aleve, but this was a once-a-year occurrence. And wow, with the pain gone, I was a new woman! While I was feeling like new, two friends (understandably) dropped out at this point. We quickly said goodbye and carried on.

At mile 23, we picked up a friend by the ballpark who had made three batches of chocolate cookies (one infused with almond, one with orange, and one with mint). This was a great pick-me-up and morale booster. It was also interesting at this point to enter into the more touristy areas of the city —like the Ferry Building (where we picked up another friend and I chugged a full bottle of almond milk), the Embarcadero, and Fisherman’s Wharf.

We continued along Crissy Field, losing two friends, and continuing on to the Golden Gate Bridge Plaza. I am very familiar with these areas of SF, so I knew what to expect, and that was comforting. As we approached Lands End (mile 35), I gritted my teeth a bit, realizing I’d have to climb a number of stairs, but I took some acetaminophen and powered through — knowing the end was in sight. My mood was brightened by seeing a young coyote on the trail.

The mood stayed positive as we reached Sutro Heights and watched the sunset from the parapet. We continued along Ocean Beach, watching bonfires light up near the water. At one point as we reached Sunset Dunes, it strangely felt more comfortable to run(?!?!), so we jogged for about a half mile. We then made it into Fort Funston, our last stop! As my shoes filled with sand on the wild dark dunes, we headed uphill and then downhill to where we had started our day. After 14 hours, we were done! 

This hike felt like such an accomplishment, but it was also seriously mentally and physically exhausting. I’m not sure I’ll do it in its entirety again, as I was still sore for a few days afterward!

Now that I’ve done the hike, here are my recommendations if you want to take on this crazy route for yourself.

1. Bring your own food. Keeping stops to a minimum is important. Mission Blue and the Ferry Building are great for picking up food, but keep it quick.
2. Keep your pack light. Only carry what you need. Do bring a headlamp for darkness and a bottle of water, but you can refill easily on the trail instead of lugging 3 liters from the start. 
3. Do bring an extra pair of socks and some first aid supplies in case of blisters. I swear by Wrightsock and my feet were great all day! 
4. The best times of year to do this hike are when there is a lot of daylight. While you can do this trail any time of year, between March and October is best. 
5. Take preventative pain meds. Unless you are Superman or Superwoman, you will likely need some pain medication. I took some before I started hiking and then every six hours thereafter. With pain meds, it is extremely important to stay hydrated!! 
6. I said this before, but don’t stop unless necessary! If you stop for lunch — or anything — you may not finish due to time or your body stiffening up.
7. Bring friends for moral support. Chatting with good friends for 40 miles helped! People can drop in and out of the hike as they like, so make sure friends know they don’t have to do the whole thing.
8. Enjoy! You may never walk this many steps again in a day, so relish this experience. If you need to quit early, there is no shame in that! Protect your body and stay safe out there!

 

1.