Have you seen the Barbary Coast bronze medallions in the sidewalk while walking through San Francisco? Did you ever wonder what it was all about? We did! The hubs and I followed 170 bronze medallions along the Barbary Coast Trail to see more than 20 historic sites and parts of San Francisco we wouldn’t have given a second thought to. We learned so much about the history of the buildings and the city of San Francisco! Definitely download the Barbary Coast Trail audiobook tour and maps, it is so worth it to hear about the history of what you are seeing and experiencing along the way.
Follow the Medallions
We started the morning off at the old US mint (9:30 am). The city streets were just beginning to wake up. Not many tourists were around so we could easily listen to the story on our phone about the old mint built in a Greek revival style for the Comstock load in 1874. Thankfully for San Francisco, it survived the 1906 earthquake and the money there helped rebuild the city.
Watch for the bronze medallions on the sidewalk! The arrows point you in the direction you should be going so you can’t get lost. Hallidie Plaza was our next stop and is part of the cable car turn around that runs from Hyde street where we ended our adventure. At this stop, you will hear the story of Andrew Hallidie, developer of the first cable car. Pass the cable car but follow the route up to Union Square. We went during the holidays and it was all decked out with a giant Christmas tree and ice skating rink. Love the city during the holidays!
After enjoying the festivities and history of Union Square, you will find Maiden Lane down a very nice and clean alley with super fancy clothing stores. Listen to the shady story of how Maiden Lane was named…hint, women charged money for certain activities! I did love the building designed by Frank Lloyd Wright. This is noted with a small red square with his signature on it. As you leave this shady past of San Francisco, follow the medallions to the China Town Gate. This begins your extended tour through China Town.
- Hallidie cable car turn around
- China Town gate
- follow the medallions!
- Frank Lloyd Wright building
- Frank Lloyd Wright building
- Union Square
While walking through China Town you really feel like you have entered a whole new era. The blend of the old with the new is fascinating! Loved the red lanterns strung across the streets! Don’t forget to look down the alleys for some amazing art along the walls! We stopped at Old Saint Mary’s Church and went in to check out the photo display of the 1906 earthquake. It is a testament to the masonry dudes for building something that can not only withstand a large earthquake but also that survived the fires that came after! A nice church volunteer showed us the photo display just before the service started.
- Old St Mary’s Church
- Alley!
- Lanterns lining the streets!
The next part of the adventure takes you further into China Town to Waverly place known as the painted balconies. Here we listened to the history of the Tong’s and the battle of 1875. If you look up, you might see people airing their clean laundry. We giggled a little like schoolkids since it was also undies! Don’t hold it against us! We are very sheltered in our suburb! 🙂 Just down the way, we found ourselves in front of Tin How Temple. This was the first Chinese temple in the US. We opted not to go in this time but admired the architecture on the outside. We really needed to do this trail in 3 segments to truly experience it.
Ross Alley is home to the Golden Gate Fortune Cookie Company! We stopped in and saw them still using antique fortune cookie machines. The smell was so delicious! The hubs walked out with a bag of cookies! There were young kids practicing some sort of martial arts in the alley. So great to stand and watch, just stay out of the way of their swords! Need to make a phone call? Head over to the old Telephone Exchange next! It is now a bank but the pagoda-style building stands out so you can easily find it. The ladies that worked the exchange had to know over 1200 numbers by name! Yikes!
- China Town streets
- Making fortune cookies
- Tin How Temple
Next up is Portsmouth Square. This used to be the center of the city before they filled in Yerba Buena Cove. I knew there had been some landfills done but this was a crazy amount and we now have so many high rise buildings built on this! Kudos to the engineers back in the day. We have tons of technology to help us figure this out, they had just their brains and strong backs! From here we walked down Commercial Street toward the old shoreline. We all know what the TransAmerica building looks like but do you know the history? Something about Mark Twain and a firefighter. Listen to the audiobook and you’ll find out!
In the shadow of the high rises, we found ourselves in front of the Belli Building. This place has a lot of history from the performers that made their start there to the lawyer Belli who shot off small canons from the rooftop! This was probably the cutest old building we stopped at. I love the old architecture. I know it isn’t as old as back east but it is old for us here! When you reach the Hotaling Buildings you will have a great view of the TransAmerica building between the buildings. Also, note the curvy part of the path between the buildings. This is where the old shoreline was prior to it being filled in! Our next stop was a coffee shop with delicious coffee and hot chocolate as well as a much-needed restroom! The day was getting cloudy and was trying to rain so having a hot beverage was nice!
- Commercial Street
- Squiggly line = old shoreline
- view from the coffee shop
Unfortunately due to time and weather we skipped a few sites, which we want to go back to, and spent a little more time in the alley between Vesuvio Cafe and City Lights books. Had I known this is also where the underground tunnel was we would have explored that too. Next time! The beat was a big part of our history as a country and as Californians and I feel like it was skipped over when I was in history class. Thankful these places are preserved so we can still experience it!
Keep following the bronze medallions to Washington Square. No, this park isn’t square and it has a statue of Ben Franklin in it. Super confusing right? It’s all explained in the audio tour. Enjoy a rest here before you head up Telegraph Hill to Coit Tower. We got a little confused with the medallions but knew we were going to end up at Coit Tower and we could clearly see it so we ended up going up Filbert Street which was the back entrance. Sort of thankful we did this as the other way was a million steps!
- view from the top of the steps on Filbert St
- Washington Square
- Vesuvio Cafe (the beat)
I had been wanting to take the tour of Coit Tower for some time now and this was my opportunity! We walked around and admired the hand-painted murals of California’s past and purchased our tickets to ride the elevator up to the top. The day we were there happened to be sort of busy so it was about a 30-minute wait to get on the elevator. The views were so worth the wait!! There are windows in the openings at the top and some of the windows were open so I could hang out and look around. One poor lady smooshed her nose trying to look out the freshly cleaned closed window. I asked her if she was ok and when she said yes, I busted out laughing. I, of course, apologized for the laughter but did continue to giggle. Kharma will definitely get me back for that one!
- the hubs and bosslady
- view of the city
- Coit Tower
- look up!
- views in all directions!
- view of the bay from Coit Tower
There were no bronze medallions guiding us, that I could find, so we walked down a very long set of stairs. I believe these are the ones that we would have walked up if we went the other way. I would not want to live in those homes and have to take up groceries. After your legs have stopped shaking from the climb down, cross over to the Embarcadero. We have walked this from the Ferry Building to Crissy Beach a few times so not much new stuff for us to see. Hindsight, we should have jumped in the rickshaw and had them take us to Ghirardelli Square and saved some time and wear and tear on our tootsies!
Since EVERYONE wants to ride the historic cable cars, the line was quite long and took over an hour to just get on the cable car. Thankfully it was time enough for me to leave the hubs in line while I dashed over to Ghirardelli square super quick! He hadn’t moved more than 10 feet in line by the time I got back. We had great people near us and we were all super excited to watch the cable cars turn around and see the joy of everyone getting on…just kept wishing it was us! Once we finally made it on I got to hang off the side! So. Much. Fun!!!!!! Taking the cable car through the city streets as the sun was setting was just magical. We reached Union Square and it was all lit up beautifully and people were singing in the streets. Seriously couldn’t have been a better end to a really long day wandering the city!

Happy Cable Car riders!
We ended up back at the parking garage at 5:30 pm. 8 hours of exploring on hard concrete was difficult on the body but so wonderful for the soul! I would highly suggest doing this adventure in the 3 parts that the audiobook tour is broken down in. Or maybe spend the night in the city so you can see everything!
The hubs and I both agree that having the map and the audiobook as our guide was well worth the $25 we spent on downloading it. It gave us so much more information than we would have had if we would have just followed a free map. It was really well put together! We do not receive any kickbacks for this, we found it online and gave it a try and it did not disappoint. You can find the Barbary Coast Trail download here.
Things We Love:
Hiking our way through the city was so much fun but we didn’t want to look like typical hikers, or how we usually do out on the trails, so it’s handy to have a jacket that is both stylish and built for performance. The bosslady is wearing her Christmas present in the above photo! The Prana Martina jacket. It’s super comfy soft on the inside, fits like I am actually a woman, and is water-resistant. So great to have in foggy San Francisco! It is my go-to jacket for outings like this!
Where else can you find us?
Check out our short YouTube video of our adventure here: