You’ve walked down Market Street a thousand times. You see the tourists huddled toward Union Square or the techies sprinting toward the Salesforce Tower. But if you take a sharp turn right at the Palace Hotel, you hit a stretch of asphalt that feels like a glitch in the city’s grid. It’s only two blocks long. Seriously. It just... ends.
But New Montgomery St San Francisco CA isn't just a dead-end mistake. It’s arguably the most architecturally dense, historically heavy, and "vibe-rich" slice of the city that most people just overlook. Honestly, if you want to understand how San Francisco went from a muddy gold-rush outpost to a global tech hub without losing its mind, you have to walk these two blocks.
The Man Who Tried to Move the Center of the Universe
To understand why this street exists, you have to talk about William Ralston. The guy was basically the Tony Stark of the 1870s. He founded the Bank of California and decided that the city’s "Financial District" was getting too cramped. His grand plan? Extend Montgomery Street south, past Market, and turn the "South of Market" (SoMa) area into the new posh center of town.
It didn't quite work.
He managed to carve out these two beautiful blocks, but then he hit a wall. Literally. Two wealthy property owners on Rincon Hill—Governor Milton Latham and a shipping tycoon named John Parrott—basically told him to get lost. They refused to sell their mansions to make way for his road.
Then, in a twist straight out of a noir novel, Ralston’s banking empire collapsed. He went for a swim in the San Francisco Bay and never came back. Some say he drowned; others say he just couldn't face the music. Either way, his dream of a massive thoroughfare died with him, leaving us with this weird, gorgeous stump of a street.
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The Art Deco Giant You Can’t Ignore
If you’re standing on New Montgomery today, your neck is probably tilted back. You’re looking at 140 New Montgomery.
For a long time, this was just "The Telephone Building." Built in 1925, it was the city’s first real skyscraper. It’s a 26-story Art Deco masterpiece that looks like it belongs in Gotham City. The architect, Timothy Pflueger, was obsessed with a design for the Chicago Tribune Tower that never got built, so he basically said, "Fine, I’ll do it in SF."
Look closely at the top. See those giant eagles? They aren't just for show. Back in the day, the roof was used to fly a 25-foot red flag to warn sailors of incoming storms.
Expert Tip: Walk into the lobby. It’s free. You’ll see a ceiling inspired by Chinese brocade and images of phoenixes and unicorns. It’s easily one of the most beautiful interiors in the Western United States, and yet most people walk right past the front door.
Winston Churchill actually visited this building in 1929. He made his very first transatlantic phone call from right here to his home in London. Kinda wild to think about while you’re standing there checking your 5G signal.
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Where to Eat (and Where the Locals Actually Go)
New Montgomery is a weird mix of old-school "suit and tie" and "start-up casual."
If you want the full-blown, "I just made a million dollars in 1890" experience, you go to the Palace Hotel. Specifically, the Garden Court. It’s got a leaded-glass ceiling that cost a fortune even back then. You can get afternoon tea there, but honestly, the Pied Piper Bar around the corner is where the real stories are. It’s named after the massive Maxfield Parrish painting behind the bar.
But if you want something that feels like 2026, things are changing. Street Taco just moved in at 126 New Montgomery, bringing that Mexico City street food vibe to the Financial District. It’s fast, the tortillas are organic and handmade, and the al pastor is legit.
- The House of Shields: Directly across from the Palace. No signs. Just a big wooden door. It’s one of the oldest bars in the city. Legend has it there used to be a tunnel connecting it to the Palace Hotel so high-society men could sneak over for a drink (and other things) without being seen on the street.
- Academy of Art University: Their main campus is tucked in here, so you’ll see students with portfolio cases mixing with Yelp employees (Yelp’s HQ is in the 140 building).
- Mourad: A bit further down, but if you want high-end Moroccan food that will blow your mind, this is the spot.
Is New Montgomery Safe in 2026?
Let’s be real. San Francisco gets a lot of bad press. You’ve seen the headlines.
But New Montgomery is a bit of an anomaly. Because it’s anchored by the Palace Hotel on one end and big tech offices on the other, it’s one of the most well-monitored and "clean" feeling streets in SoMa. It’s active. There are people out for dinner, hotel guests, and security.
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That said, it’s still SF. Don't leave a bag in your car. Don't even leave a jacket in your car. Smash-and-grabs are still a thing in 2026, though the city has been cracking down on the Belden Place and New Montgomery corridors to keep the "Financial District momentum" going. Stick to the main lit areas at night, and you’ll be totally fine.
Why You Should Care
New Montgomery is a survivor. It survived the 1906 earthquake (well, the street did; the buildings had to be rebuilt). It survived the dot-com bust, the 2008 crash, and the pandemic.
It represents the "Pivot" of San Francisco. It’s the bridge between the old-world luxury of Market Street and the gritty, innovative future of SoMa.
Actionable Ways to Experience New Montgomery Today:
- The 15-Minute Architecture Tour: Start at Market and New Montgomery. Look at the Palace Hotel (Renaissance Revival), then the Sharon Building (1912), then 140 New Montgomery (Art Deco). It’s a century of history in 100 yards.
- The Hidden Garden: 140 New Montgomery actually has a private-ish courtyard garden. If you can slip in during business hours, it’s a silent oasis in the middle of the chaos.
- The Cocktail Trail: Start with a martini at the Pied Piper, then cross the street to House of Shields. It’s the fastest way to feel like a 1920s power broker.
The next time you’re in the city, don't just follow the crowds toward the Ferry Building. Turn onto this two-block "mistake." You’ll find more history per square inch than almost anywhere else in California.