You’re walking around downtown Pittsburgh looking for something different, something most tourists (and even a lot of locals) completely miss. Your phone GPS keeps saying “arriving at destination” while you’re standing in the middle of a busy road staring at a brick wall. That’s exactly how most people first meet Try Street. It’s not a typo, and it’s not street food. It’s a narrow, covered passageway that feels like someone forgot to delete it from the city map. Ready to go find it with me?
Key Takeaways
- Try Street is a real, one-block alley hidden under a giant railroad bridge downtown.
- It’s tied to Lewis & Clark, the first steamboat on the Ohio, and a forgotten hanging in 1856.
- The huge 1921 warehouse next to it is now luxury apartments with a hidden bar and bowling alley.
What Exactly Is Try Street?
Most maps don’t even show it properly. Try Street is a single block that runs underneath the Panhandle Bridge, running from First Avenue down to Second Avenue in the Central Business District. It’s only about 20 feet wide and completely roofed by the railroad tracks overhead, so it always feels like a tunnel.
Here’s the easiest way to find it in 2025:
- Start at the Wood Street T station
- Walk toward the river on Liberty Avenue
- Turn right just before the big gray bridge
- Look for the giant “Terminal 21” sign – you’re there
Pro tip: If you blink, you’ll walk right past the entrance.
200+ Years of History in One Block
This little alley has seen some serious action. Back in 1803, Meriwether Lewis stopped here to have a 55-foot keelboat built for the famous Lewis & Clark expedition. Eight years later, the very first steamboat to travel the Ohio and Mississippi rivers (called the New Orleans) was also constructed on the same spot.
By the 1830s, the area was nicknamed “Hardscrabble” because poor Irish and German immigrants built shanties along the muddy ravine. In 1856, a massive fire ripped through, and a man named John Tiernan was hanged right on Try Street for murder – one of the last public executions in Pittsburgh. Underneath it all flows Suke’s Run, a stream that’s now buried in a sewer but used to flood the whole neighborhood every spring.
By the late 1800s, this block was part of Pittsburgh’s pork-packing district. They called it “Porkopolis” because more hogs were processed here than almost anywhere else in America.
Try Street Terminal: From Warehouse to Luxury Lofts
In 1921, they built the massive Try Street Terminal – a ten-story concrete warehouse that takes up a whole city block. It was designed to load train cars directly from the bridge overhead. The building is on the National Register of Historic Places because of its rare “mushroom column” construction.
Fast-forward to 2021–2024: developers turned it into 205 super-cool apartments called Terminal 21.
What you get if you live there today:
- Exposed brick and 14-foot timber ceilings
- A rooftop deck with river and skyline views
- Duckpin bowling alley in the basement
- A speakeasy-style bar hidden behind a bookcase
- Gym, dog wash, and package lockers
Rent in 2025 runs about $1,800 for a studio to $3,500+ for a big two-bedroom. Parking is extra (and painful).
How to Visit Try Street in 2025
Best route (takes 8 minutes from Market Square):
- Walk down Liberty Avenue toward the river
- Pass the big gray Panhandle Bridge on your right
- Look for the arched opening with a “Terminal 21” banner
- Step inside – welcome to Try Street!
Photography tips from someone who’s been there a dozen times:
- Blue hour (right after sunset) is magic – the bridge lights up orange
- Bring a wide-angle lens; it’s tight in there
- Stand in the middle and shoot straight up for that “secret tunnel” vibe
Safety note: It’s darker than a normal street, but security cameras and residents are coming and going 24/7. I’ve walked it alone at 10 p.m. with zero issues.
Why Try Street Feels Forgotten (And Why It Isn’t)
Back in the 1980s, city planners almost wiped it off the map during highway construction. A 1983 newspaper article even declared, “Try Street no longer exists.” Luckily, preservationists fought back.
Today, it’s safer and cleaner than it’s been in a century, but most Pittsburghers still don’t know it’s there. That’s what makes finding it feel like discovering treasure.
Living at Terminal 21: The Honest Review
I talked to a few residents in 2024–2025. Here’s the real scoop:
The good stuff everybody loves:
- Walking to Penguins and Pirates games in 10 minutes
- Giant windows and insane character
- Quiet inside despite trains overhead (they’re surprisingly not loud)
The complaints you’ll see in reviews:
- Management can be slow to fix things
- Paid parking starts at $175/month
- Some units get train vibration on higher floors
If you love old buildings and don’t mind city quirks, people say it’s worth it.
7 More Hidden Streets & Alleys in Pittsburgh
Once you’ve found Try Street, keep exploring:
- Sugar Top – a staircase neighborhood with no real streets
- Rising Main Steps – 300 steps straight up the hill
- Voodoo Way – tiny alley behind a brewery in Lawrenceville
- Mexican War Streets steps – colorful houses and secret passages
- Fort Pitt Block House tunnel – actually goes under Point State Park
- Joncaire Street – feels like Europe with its narrow cobblestones
- Strawberry Way – downtown alley full of street art
Conclusion
Try Street may look like an ordinary walkway today, but once you know its past, it becomes one of Pittsburgh’s most fascinating hidden gems. From buried streams and legendary explorers to early steamboats and gritty 1800s neighborhoods, every step carries a story. Visiting this spot isn’t just about taking photos — it’s about standing in the middle of history that most people walk past without noticing. Whether you’re a traveler, a photographer, a history lover, or simply curious about the city’s forgotten corners, Try Street gives you a rare chance to see Pittsburgh from a whole new angle. Take a moment there, look around, and imagine the world that once existed beneath your feet.
FAQs
1. Where exactly is Try Street located in Pittsburgh?
Try Street sits in Downtown Pittsburgh, tucked between First Avenue Station and the newer Terminal 21 apartment complex. Many visitors don’t notice it because it appears more like a walkway than a traditional street. You can enter from the bike path near the First Avenue Garage or from the ramp beside Terminal 21. Once you’re there, you’ll see rail tracks, the bridge curve, and the narrow corridor that gives the area its hidden feel.
2. Why is Try Street historically important?
Try Street is built directly over Suke’s Run, one of Pittsburgh’s buried streams. This area also connects to major moments like the Lewis and Clark expedition, the first steamboat test by Nicholas Roosevelt, and the old Hardscrabble neighborhood, which was once known for crime and poverty. Because so much early Pittsburgh activity happened around this spot, the street carries layers of forgotten history that you can still sense when you walk through it.
3. Is Try Street safe to visit?
Yes, Try Street is generally safe during the day, especially since the area has new buildings, lights, and foot traffic from the bike path. However, like many narrow and quiet city corners, it can feel isolated at night. Most visitors prefer coming during daylight hours, especially if they plan to take photographs or explore the surrounding streets.
4. What makes Try Street popular on social media?
The curved bridge, the exposed rail tracks, the old brick walls, and the sudden opening toward the river create a naturally dramatic backdrop for photos. Many influencers and photographers use it for cinematic shots because the location looks like a movie set — urban, rustic, and mysterious. Its combination of shadow, perspective, and texture makes it perfect for portraits and street photography.
5. Are there other hidden or historical spots near Try Street?
Yes! Within a short walk, you can visit several interesting places:
- The Monongahela River bike trail
- The First Avenue open-air train platform
- Site markers connected to Lewis & Clark
- Historic bridges and old industrial structures
- The Duquesne Incline overlook (a bit further, but worth it)
Exploring this area is ideal for anyone who enjoys old architecture, secret corners of the city, and the quieter parts of Downtown Pittsburgh.
