4 Unique Pittsburgh Streets to Visit in the City

Published by Jeremy. Last Updated on July 10, 2022.

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When we talk about Pittsburgh streets, it is often followed up with how terrible it is to drive on them. We get it, we all stink at driving here (with no added thanks to the roads), but we're not going to talk about that here.

One thing we have found interesting in our exploration of Pittsburgh is not just how bad the drivers are, but rather how many unique streets this city has!  Between our downtown roads being designed on a triangular grid and the outer neighborhoods being full of hills, many roads in this great city are unique to say the least.

After countless trips out and about in the city, the following is a collection of our favorites that we've visited so far.

The Street With a Billion Dollar View – Grandview Avenue in Mount Washington

Pittsburgh Skyline from along Grandview

We can't start any list of the most unique roads in the city without featuring the one with the best view: Grandview Avenue on Mount Washington!

Okay, you probably know enough about Grandview that our feature of it here isn't that special.  You love it, we love it, and as far as Pittsburgh roads goes, it is unanimously considered one of the best.

When it comes down to a list of unique roads in the city, this one has to show up because it has the most beautiful viewpoints in the city.  

By the Monongahela Incline at Station Square you get a wonderful view of the skyline while being perpendicular to the city, and a mile down the road at the Duquesne Incline you are able to take in the city at its most beautiful angle with the three rivers and skyline being a star attraction!

Now that we have that one out of the way, it is time to get to a few you may not know about!

After visiting Grandview, why not grab a drink at The Summit on nearby Shiloh Street?

The Street Made of Wood – Roslyn Place in Shadyside

Roslyn Place in Shadyside

Did you know that Pittsburgh is home to one of only a few remaining wooden streets in the USA? It is true! Roslyn Place in Shadyside (off Ellsworth Avenue) is comprised entirely of wooden blocks that are arranged end over end much like the more common cobblestone roads we know today.

As the history goes, in the 1800s wood streets were quite popular as wood was abundant and was favored over its cobblestone counterparts.  Although a great idea and a beautiful design by today's standards, wood roads do not last nearly as long as stone, brick, and asphalt, and they fell out of popularity as other styles rose in prominence and reliability.

It doesn't take long after you arrive to Roslyn Place for you to realize why this one survived- the road itself is quite small and is even somewhat easy to miss.  If you're like us, you probably drove by this one countless times and didn't even notice it was there.  

In any case, do yourself a favor and stop by for a quick visit the next time you're in Shadyside to check out this very unique street in the city!

After checking out Roslyn Place, head over to Millie's Ice Cream for a scoop of one of their delicious creations!

The Steepest Street in the USA – Canton Avenue in Beechview

Canton Avenue in Pittsburgh

We all know that Pittsburgh is a hilly place, but what you may not know is that Pittsburgh is home to the steepest publicly accessible road in the USA (and possibly even the world!).

Canton Avenue in Beechview features a hill with a 37.5 percent grade, making its short, roughly 100 foot length one for the record books.  

This road does not look like much from the ground, but a quick drive up the road reminds you that this is one hill not to mess with- it is steeper than it looks!

Canton Avenue in Beechview

I'm not going to lie, we were going to be brave and try and drive down the hill as well, but the combination of the posted Do Not Enter sign and watching another car go down it illegally turned us away from making the attempt. With a drop-off that looks like a roller coaster hill, I'll go ahead and take the long way down- thanks.

After making your way up Canton Avenue, grab a slice of local favorite Beto's Pizza just around the corner.

The Street Made of Stairs – Yard Way in South Side Slopes

Yard Way in Pittsburgh's South Side Slopes

If it has a street sign, it counts as a road- right?  If you agree, much like the city does, then the South Side Slopes side streets are for you. This Pittsburgh neighborhood is home to dozens of named staircases that are used to navigate the steep hillside where car-carrying side streets are impossible.  

So if you're looking to check out the views in this unique part of town, you better be prepared for a bit of a climb!

Pittsburgh from the South Side Slopes

One of our favorite staircases to climb is Yard Way which traverses almost the entire hill in one straight shot (minus one block at the bottom connecting S 18th Street to Pius Street just a few feet away).

Throw in a few nearby roads and other staircases on your way down and you'll have an outing full of several gorgeous views of the city as well as many, many steps to climb in this neighborhood's unique street setup.

When you're done working up an appetite on the slopes, head over to La Palapa for some delicious Mexican tacos!

Do you have a favorite street in Pittsburgh that is not featured in this list? Comment below to tell us about it! We'll visit, and if we like it we may even add it onto this list!

For more things to do in Pittsburgh, click the previous link to check out our recommendation of 365+ unique things to do in the city! Or if you want to find something cool in a neighborhood near you, check out our guide to the 90 Pittsburgh neighborhoods!

23 thoughts on “4 Unique Pittsburgh Streets to Visit in the City”

    • I have to add a few more gems to the list of “unique” streets of Pittsburgh. Ever drive up Capital Avenue in the South Hills? it is a steep vertical climb over several blocks entirely comprised of cobblestone…OMG. I expect the axels on my SUV to break every time I go over 15 mph on that hill.

      The other I am thinking of is Sycamore heading up to Mt. Washington….hairpin turns all the way up.

      Yes, the views are spectacular, but really test your vehicles fortitude. Getting there is half the fun!

      • Oh yeah! We used to live on Sycamore on the top of Mt. Washington, so we’re quite familiar with that road. There are also several good cobblestone roads with inclines over in the North Side too. Not that I enjoy driving my car on them, you sometimes have to.

      • Also, William street, very nearby Sycamore, in Mt Washington is beautiful, or at least it used to be a very quiet, steep, woodshed road that winded up the mountain; I loved to climb it with my dog.

      • I lived in Beechview and walked up and down Capital Ave in Brookline everyday going to high school. Not only is it steep and cobblestone but it also has an almost 90 degree turn at the bottom.

    • I lived on Bothwell St on the northside. If you came off the East Street Valley Expressway onto Milroy, you came to a 90degree turn to the right or if you went straight ahead as many 18 wheelers and tour busses did – you came to steps. On the city maps, there was no indication of that.
      Bothwell was a steep grade and it had a hair pin curve to the left and the grade there had to be 50% at least. It was fun watching the road crew the day they paved it!

  1. Those named stairways mess up the GPS so bad! Always better to ask a local for directions in some of these city neighborhoods. Super interesting about Roslyn Place, too. Think I’m going to have to go make a visit!

    • That’s so true. Navigating around Pittsburgh is difficult even with a GPS. That is why I think the best way to get around the stairs in the Slopes is to park at the bottom and walk a bit rather than trying to drive to where you want to go.

      • It’s so steep that when you’re at the top to go down, all you see is the front of your car…….until it tips over the edge.

  2. A couple of oddities I wish they had mentioned:
    * Two parallel streets downtown cross at a right angle (5Ave, 6Ave). Explain that to someone from Manhattan.
    * Beechwood Blvd intersects Monitor Street in three places.
    * Irwin Ave on the North Side exists in four disconnected sections.
    * South Side Avenue is on the North Side, but South Main Street is in the West End.
    * You cannot use Blvd of the Allies in Oakland to get to Blvd of the Allies downtown.
    * Saline Street in Squirrel Hill has nothing to do with Saline Street in Four Mile Run, a half mile away, though before the Parkway East was built, they were one continuous street.
    * The Central stop on the South Busway can only be accessed from one of two staircases with over 100 steps each.
    * There are over 700 of those staircases. Don’t laugh — they’re often the fastest way to get you from Point A to Point B.

    • Stuart, I think 5th Ave. meets 6th St. From Liberty Ave. to the Allegheny are Streets. From Liberty to the Monongahela are Avenues.

      • St Michael street southside. It used to be unaccessible by car and it had grass, picnic tables and a marble board in the middle of the street.

  3. I think there are others, but Stella St in Southside is a “split-level” with each lane of traffic at a different elevation and a wall in between!

  4. In the early 50’s we lived on Bailey Ave. across the street from Grandviiew Park. Wonderful view of the rivers , downtown and the mills at night. Took the incline up and down to Carson Street, walked across the bridge to Smithfield St. to the offices in the Gulf Bldg. Froze in the wintertime. Went to Pitt at night and Saturdays on the trolleys. Sidewalks and streets up from Warrington to Bailey and to Duquesne Heights a challenge. Narrow, hilly and rough.

  5. Check out Cutler St off Perryville Ave. A great place to slide on some cardboard boxes when covered with snow in winter time. Hours of enjoyment as a kid. Can drive down in nominated time ,but never saw anybody drive up. You will see what I mean.

  6. I grew up in Forest Hills at 15 Hillcrest Road. It is the highest spot in Allegheny County. The back side of Hill crest is so steep, cars do not usually travel in it in winter, even when clear of snow. If you put your brakes on with only the slightest amount of gravel or slag ( ashes) you will slide all the way to the bottom. The house at the bottom of the hill has been hit numerous times over the years. Go see it. But, be really careful if you go down it. I think IT is the STEEPEST in the USA.

    • How to get to Hillcrest Road. Go Parkway East thru Squirrel Hill Tunnel. Get Get off at Ardmore Blvd.( Rt. 30 east). Go three stoplights and make left at Braddock Road( there’s a stone bus shelter built in the ’30’s by the WPA on the right as you turn). Go up the hill and come to a ” Y”. Stay left on Glasgow Rd. Follow all the way to the top and take the third or 4th Street to the left on Hillcrest Rd. I lived in the last house on the right(15) before the steep hill. I would have measured the angle of steepness, but don’t know how to do it accurately. When I was young, my mother would not even let me WALK down the backside of Hillcrest. Take a ride, you’ll see why Forest Hills is on of Pittsburgh’s hidden gems of neighborhoods in the whole Eastern suburbs.

  7. It’s not the drivers that are bad in Pittsburgh, it’s the streets themselves. If they aren’t under construction, it’s that a lot are one way. Even people who have lived in the ‘Burgh all their lives find it difficult to navigate.

  8. Buena Vista St. It runs from lower North Side up to Perrysville Ave. I used to drive my college roommates who came from level cities on it to scare them. Love Pittsburgh. Now live in slower lower Delaware – yuck!


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