You've probably walked right past 106 W Church St if you've ever spent a night out in downtown Orlando. It’s one of those spots that feels like it’s been there forever, even as the skyline around it sprouts new glass towers and luxury apartments every other month.
Honestly, downtown Orlando is a weird place. One block is a sterile corporate lobby and the next is a 19th-century brick facade that smells like spilled bourbon and history. 106 W Church St sits squarely in that second category. It’s part of the historic fabric of the Church Street District, a zone that has seen more "rebrandings" than a washed-up pop star. But underneath the neon signs and the shifting tenants, there is a real story about how Orlando tried—and often struggled—to build a soul that wasn't owned by a mouse.
The Reality of the Church Street District
Location is everything. If you look at a map, 106 W Church St is nestled right in the middle of the historic block between S. Garland Ave and S. Orange Ave. This isn't just any street. It’s the heart of the original Orlando.
Back in the late 1800s, the railroad was the lifeblood of this area. The Old Orlando Railroad Depot is just a stone's throw away. For decades, this specific stretch of Church Street was where the city actually happened. It wasn't a tourist trap yet. It was just... the city. Then came Bob Snow in the 1970s. He created Rosie O'Grady's Flying Circus and basically invented the "entertainment complex" model that Disney eventually copied with Pleasure Island.
Why 106 W Church St Stands Out
While larger venues like the Cheyenne Saloon took up the massive footprints, the smaller addresses like 106 W Church St provided the texture. These are the narrow, high-ceilinged spaces that allow for intimacy. You can feel the age of the building the second you walk in. The brickwork isn't a "rustic" veneer from a home improvement store; it’s load-bearing masonry that has survived a century of Florida humidity and hurricanes.
Currently, the space is widely recognized as the home of Cahoots.
If you haven't been, Cahoots is basically the grown-up version of the arcade you loved as a kid, but with better lighting and much better drinks. It’s a craft beer bar that doubles as a retro arcade. It’s part of a larger ecosystem of nightlife spots including The Basement and The Attic. This "cluster" strategy is how these historic buildings stay viable. By sharing entries or ownership groups, they create a destination within a destination.
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It works. People go there for the nostalgia of Ms. Pac-Man or Galaga, but they stay because the atmosphere of 106 W Church St feels authentic in a way that the newer developments at Creative Village or Lake Nona just don't. You can't fake the "settled" feeling of a building that’s been standing since before the invention of the airplane.
The Architecture of the 1920s
The building at 106 W Church St is part of a row of structures that mostly date back to the Florida Land Boom of the 1920s. This was a wild time. People were buying land sight unseen, and downtowns were exploding with Mediterranean Revival and Commercial Brick styles.
Look at the windows. Look at the way the light hits the upper floors. These buildings weren't designed by computers; they were built by masons who understood that Orlando gets incredibly hot. High ceilings weren't a luxury; they were a necessity for heat management before HVAC systems were standard.
- Masonry: The red brick is iconic to the district.
- Narrow Footprint: Many of these units are deep but narrow, reflecting the way property was subdivided to maximize street frontage for shops.
- Transom Windows: You’ll see these above many doors in the area, designed to let air circulate even when the main doors were closed.
There’s a specific kind of "urban grit" here. It’s not dirty, but it’s worn. The sidewalk is uneven. The bricks have chips. For some people, that’s a turn-off. But for anyone tired of the sanitized, plastic feel of modern "Lifestyle Centers," 106 W Church St is a relief. It’s real.
What People Get Wrong About Downtown Orlando Nightlife
Most people think downtown is just for college kids from UCF or tourists who got lost on their way to International Drive. That’s a mistake.
Places like 106 W Church St cater to a very specific local crowd. These are the people who work in the law offices on Magnolia, the tech startups in the Exchange building, and the creative agencies nearby. They aren't looking for a $20 cocktail with a sparkler in it. They want a solid tap list and a place where they can actually hear their friends talk.
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Cahoots, specifically, has leaned into the "low-stakes fun" vibe. There’s something remarkably grounding about playing a game of Skee-Ball with a local IPA in your hand while the SunRail train rumbles by just outside the door. It’s a reminder that Orlando is a functioning city, not just a theme park annex.
The Impact of the Amway Center (Now Kia Center)
The proximity to the Kia Center (formerly Amway) changed everything for this address. When there’s a Magic game or a massive concert, the gravity of the city shifts toward Church Street. 106 W Church St becomes part of the "pre-game" ritual.
You see a weird mix of people. You’ve got jerseys and face paint standing next to people in business suits, all crowded around the same vintage arcade cabinets. It’s one of the few times the city's different social circles actually collide.
The Struggle for Preservation
It hasn't all been easy. The Church Street District has died and been reborn at least four times in the last forty years.
There was a period in the early 2000s where this whole block felt like a ghost town. The big "destination" draws had closed, and the city was struggling to figure out what to do with these aging buildings. Maintaining a structure like 106 W Church St is expensive. You’re dealing with old plumbing, electrical systems that were never meant for modern kitchens or high-draw arcade machines, and strict historic preservation codes.
The fact that it’s currently a thriving bar and arcade is a testament to the "adaptive reuse" movement. Instead of tearing it down for a parking garage, developers and business owners realized the value was in the vibe.
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Planning Your Visit
If you’re heading to 106 W Church St, don't just drive there and expect easy parking. It’s downtown.
- Parking: Use the Garland Lot or the 55 West garage. Expect to pay $10-$20 depending on if there’s an event.
- The Vibe: Cahoots is usually chill on weeknights but gets packed on Friday and Saturday. If you want to actually play the games without waiting, go on a Tuesday.
- The Beer: They focus heavily on Florida breweries. Look for stuff from Ivanhoe Park Brewing or Crooked Can.
- The Secret: The building is interconnected in ways that aren't immediately obvious. Sometimes you can flow between the different concepts (like The Basement) depending on the night and the door policy.
The Future of the 100 Block
What’s next? Orlando is densifying. There are thousands of apartment units planned within a half-mile radius of 106 W Church St.
This is both good and bad. It means more foot traffic and more customers, but it also means rising rents. The challenge for places like Cahoots and the owners of these historic storefronts will be staying "cool" while the neighborhood becomes increasingly upscale.
But honestly? This building has survived the collapse of the railroad era, the rise and fall of the 80s disco scene, and the Great Recession. It’s sturdy.
Actionable Steps for the Curious
If you want to experience this slice of Orlando properly, don't just do a quick walkthrough.
- Check the SunRail Schedule: Take the train in. The station is literally right there. It turns a night out into an actual experience and saves you the nightmare of I-4 traffic.
- Look Up: When you’re at 106 W Church St, look at the ceiling and the upper walls. The architectural details tell a story about 1920s ambition that a Google search can't replicate.
- Support the Local Ecosystem: Church Street works best when you hop. Grab a taco nearby, play a round of pinball at Cahoots, and then walk over to the train depot just to see the lights.
- Verify Event Times: Before you go, check if there’s a game at the Kia Center. If you want a quiet drink, avoid game nights. If you want energy and a crowd, those are the best times to be there.
The 106 W Church St address isn't just a coordinate on a map. It’s a survivor. In a city that often feels like it was built yesterday, it’s a necessary anchor to the past.