Above ground, Pendleton is a quiet eastern Oregon town known for its rodeo, whiskey, and woolen mills. But underneath its streets, a whole different world exists—a world that whispers of saloons, brothels, secret tunnels, and even opium dens. In fact, in the 1800s, Pendleton had a population of about 3,000 with 32 saloons and 18 brothels.
When I arrived in Pendleton, I was overly excited about this underground tour. I have done these in a few other places, but nothing rivals the Pendleton Underground Tour. Fortunately, my new roommate had never been, so I had a buddy to go with. The tour begins innocently enough, leading us down into brick-lined basements and narrow passageways. That’s when it really hits you that what visitors see today is only a fraction of what once existed. While parts of Pendleton’s underground have been restored and mapped, large sections remain sealed off, collapsed, or simply lost to time. No one knows exactly how extensive the network once was—and that uncertainty reshapes how you see everything that remains.
Once underground, the air shifts—cooler, a little damp, and heavy with the sense that countless stories have unfolded in these shadows. You can almost picture the boots of miners, railroad workers, and cowboys clomping across the floorboards as they sought out cards, drinks, or company after a long day.
Much of Pendleton’s underground was created by Chinese laborers who came to the United States in the 1860s to help build the transcontinenta
l railroad. When the work moved west, many of these workers stayed and carved out the tunnels and rooms beneath the city. Life above ground, however, was far from welcoming. Chinese residents faced open hostility and were even forbidden to walk the streets during daylight hours. As local historian Shirley Iverson once explained, the prejudice ran so deep that when a cowboy shot and killed a Chinese man, his only penalty was a five-dollar fine — not for murder, but for firing his gun inside city limits.
One of the most fascinating stops is the recreated Chinese laundry. During the late 1800s, many Chinese immigrants lived and worked underground due to discrimination and safety concerns. Walking through the dimly lit space, filled with irons, scrub boards, and drying lines, it’s easy to imagine the daily grind of life here. The tour guide explained how the underground was not ju
st a place of hiding, but one of survival.
Probably one of my favorite moments was stepping into the old card rooms and saloons. Wooden tables, antique bottles, and the faint smell of history (that intoxicating mix of old wood and dust) created the perfect backdrop for the guide’s tales of gambling, fights, and fortunes won and lost in a single night.
Then comes the more notorious side of Pendleton’s past. The brothel rooms, still set up with neatly-made beds and fading wallpaper, are a glimpse into the town’s red-light district, which was once one of the busiest in the West. Stories of madams who ran successful businesses—and sometimes wielded more power than the men upstairs—add a layer of grit and respect to the narrative.
One such madam was Stella Darby, one of Oregon’s most famous madams. Born in 1902, Stella moved to Pendleton in her twenties and opened the Cozy Rooms on South M
ain Street—a brothel known locally as “32 Steps to Heaven” for the steep staircase leading up to its door. From 1928 to 1967, her business thrived in a town once filled with saloons, gambling halls, and underground tunnels. Unlike many madams of her time, Stella was known for treating her employees with respect—encouraging them to save money, get an education, and even including a chapel inside the house. She welcomed the girls from other brothels to her chapel, as they were not welcome at other churches around town. Today, a bronze statue downtown honors her legacy as one of the town’s most memorable characters—a woman who distinctively made her mark in Pendleton’s wild and complicated history.
By the end, I realized the underground isn’t just a curiosity—it’s Pendleton’s unpolished truth. While the rodeo and western flair give the town its surface charm, the underground tells the story of struggle, resilience, and human nature in all its messiness.
If you ever find yourself driving through eastern Oregon, take a couple of hours to dive below the surface—literally. The Pendleton Underground Tour is a rare experience that blends history and storytelling so well, you leave with a new appreciation for just how many lives were lived in the shadows and an intense curiosity for what else lies beneath these streets.
