The Legend Beneath Sturgis
Before The Dungeon was a bar, it was just a wild idea in the mind of Tim Conrad—a local biker with a love for skulls, flames, and true biker grit. Tired of bars that only embraced biker life during Rally Week, Tim wanted something real—365 days a year. He searched for a building with a basement until a realtor showed him an old bank downtown. The "basement" was just a crawlspace behind the vault, but something about the rock walls spoke to him. Covered in cobwebs, he crawled out and said, "This is it." In 1987, he bought the building and started digging.
1987
1988
While the dream was underground, Tim kept the main floor running as the Royal Flush Casino—complete with video lottery, pool tables, and pinball. That bar kept things afloat while he dug out The Dungeon below. With no crew and no plan, just two buckets and sheer will, Tim hauled dirt up the stairs night after night. He’d cleared enough space to open the front bar. Guests entered through a stairwell hidden in a closet, and the old vault became a quirky seating nook. It was gritty, dark, and unforgettable.
Tim didn’t plan a grand opening—he just planned to be open in time. And in the summer of 1989, The Dungeon opened its doors right as Rally Week kicked off. No soft launch, no warm-up crowd—just full throttle from day one. Tim expected a few friends. Instead, the place was packed. Word spread fast about the bar under the streets of Sturgis, carved out of rock, with a vault you could drink in and a vibe that didn’t match anything else in town.
1989
The Dungeon was a hit with bikers—but not with everyone in town. From day one, Tim’s underground bar stirred things up. It had grit, attitude, and a loyal biker crowd, and that didn’t sit well with the city. While other bars cleaned up after Rally Week, The Dungeon stayed raw year-round. The city tried to shut it down—pulling licenses, banning MC colors. Most places caved. Tim didn’t. “They’re Americans too,” he said. “Nobody is outlawed from The Dungeon Bar.” To this day, it’s the only bar in Sturgis that openly allows MC colors.
1990
By the early ’90s, The Dungeon was packed—and out of space. The gravel lot behind the bar was used for parking, but Tim had a bigger vision. In 1991, he bought the lot across the alley, tore down the house on it, and turned that into bike parking. With the original lot now free, he transformed it into The Dungeon Beer Garden. It was open air, loud music, cold beer, and room to breathe. That summer, it became a favorite hangout—and it’s remained a staple of the scene ever since.
1991
Beer bobbing kicked off in 1993 when a group from Wisconsin asked to play a game from home. Tim handed them an old pressure cooker, grabbed a busted office chair, and said, “Go for it.” The rules were simple: dunk your face in ice water and pull out a beer with your teeth—no hands, no help. Tim loved it so much he started keeping score on the wall. It stuck. The scores are still posted at the top of the stairs.
1993
The Dungeon’s wildest fight in 1995 wasn’t with bikers—it was with the city. One night after closing, a few friends were on the back deck, cracking beers and winding down. No one was being served. No one was paying. But the city called it after-hours service and pulled The Dungeon’s beer license. What they overlooked was that the deck sat outside Tim’s private apartment on the 3rd floor of the building. He fought it in court. “I didn't sell a damn thing,” he told them. One week before Rally, he won. The license came back just in time.
1995
For years, The Dungeon’s only entrance was hidden in the back of a closet—literally. You’d open the door, slip behind some coats, and descend a narrow staircase into the bar carved out of rock. It was underground in every sense of the word. But in 1998, Tim decided it was time for something bigger. He ripped out the old stairwell and built a wide, open staircase that led straight from Main Street into the heart of the bar. It gave The Dungeon a real front door—but the biggest transformation that year didn’t happen at the entrance.
Behind the bar, there was a single bra hanging on a hook. No story behind it, just something left behind. But that changed when Barbie, one of The Dungeon’s most legendary bartenders, teamed up with fellow bartender Trina and made a sign that said, “We’ll buy your bra for a dollar.” It started as a joke—just something wild to get a laugh during Rally Week. But within days, bras were pouring in. Lace, leather, neon, camo—you name it, it hit the ceiling. What began as one silly stunt turned into a full-blown Dungeon tradition.
At first, management didn’t notice. But then, one bra swung down in front of a security camera and blocked the view. The GM stormed down the new staircase, looked up at the ceiling in disbelief, and shouted,
“What the fuck did you do to the bar?!”*
Too late. The ceiling was already a riot of color, and the tradition was sealed. Since then, thousands of bras have flown overhead—each one a little piece of wild Rally history stitched into the fabric of The Dungeon.
1998
It might be gritty, underground, and rough around the edges, but that’s exactly why The Dungeon draws in people who live in the spotlight. Over the years, it’s become a low-key legend. No velvet ropes, no bottle service—just loud music, loyal bikers, and no one making a fuss if you’re famous. Dale Earnhardt Jr. signed the TV. Hulk Hogan squeezed into the low ceilings. Richard Rawlings calls it his favorite bar in Sturgis. Big & Rich became longtime friends. The Dungeon doesn’t care who you are—just that you’re here to have a good time.
2000’s
For decades, The Dungeon ran on sweat, grit, and long nights—and Tim ran it all. By 2011, Tim felt that it was time to ride more and enjoy Rally like the people he’d served for years. When considering selling, Trinity and Travis stepped in. “Don’t sell it,” they said. And in 2013, they officially became co-owners. Trinity brought fresh energy, revamping merch, drinks, Rally entertainment, and the bar’s online presence. Travis kept it steady handling repairs, maintenance, and beer runs. Tim didn’t walk away, but for the first time, he stepped back and let the next generation carry it on.
2013
Over the decades, Tim’s seen a lot change—not just in The Dungeon, but in the Rally itself. What started as raw and rebellious has become big and commercial, with sponsors, stages, and full production. Competing with that? Nearly impossible. But The Dungeon was never about keeping up. Tim made the call to open just one month a year, for Rally, when it matters most. When asked if he could write one thing on the wall forever he didn’t hesitate: “Thanks to all the friends and the unforgettable memories over the years.” Because it was never about the size of the bar. It was always about the soul of it.