Popular Pittsburgh is often asked, “What sights should I see in downtown Pittsburgh?” Rather than giving you some boring, run-of-the-mill list of landmarks, we thought we’d make it fun for you to explore the city on your own. Therefore, we created this Tour of Pittsburgh. Tag your photos with #popularpittsburgh, and we may featured you on our social media!

In addition, we also made this tour a bit of a trivia quest. For each landmark, we’ve included some information and a question. We’ll drop clues to help you find the answers. Correct answers are posted at the bottom of the page.

You can begin the tour at any of the 10 points of interest and pick up the trail from there by going to the next site. Along the way, feel free to take in the other venues. If you get lost, just ask someone for directions. Pittsburghers are a friendly lot and most will be eager to help.

The time to complete the tour will vary according to your pace and curiosity. It should take a few hours, but there is no reason to rush. Enjoy Pittsburgh.

1. The Point (Point State Park)

This is where it all began for Pittsburgh. George Washington, when he was merely 21 years old, explored this land in 1753 and recognized the area at the confluence of the Allegheny and Monongahela rivers as very strategic. From his assessment, the Virginia Colony established Fort Prince George here in 1754, but the French decided they’d like this piece of real estate for themselves and drove out the British, establishing Fort Duquesne at the site. In 1758, the Brits moved to get the land back, and under the command of General John Forbes and the governance of Prime Minister William Pitt, they marched on Fort Duquesne. Unbeknownst to the British, the French had vacated days before. The British took the land, establishing Fort Pitt.

While here, don’t forget to check out the panoramic view of the Golden Triangle and take a photo. A good location for pictures is in front of the newly renovated fountain.

Trivia:

You’d be a real BLOCK head if you didn’t check out the oldest building West of the Allegheny Mountains at the Fort Pitt Museum, which is known as what?

 

Head out of Point State Park toward the Wyndham Grand Hotel. Walk alongside the hotel on Liberty Avenue past Gateway Center to the corner, which is Stanwix Street. Cross Stanwix Street. You are now on Penn Avenue, which will lead you into the Cultural District.

 

2. The Cultural District

Located in what used to be the city’s “red-light district” is Pittsburgh’s Cultural District, which is home to renowned theaters, art galleries, restaurants, and shops. Where Sixth Street intersects with Penn Avenue, look to the left. At 101 Sixth Street, you will find the Byham Theater, which hosts a variety of performances. To the right, at 600 Penn Avenue is Heinz Hall, one of the city’s most opulent venues and home to the Pittsburgh Symphony. Further down Penn Avenue on the left, at 621 Penn Avenue is the O’Reilly Theater, the home for Pittsburgh Public Theater. At the next block on the right at 237 Seventh Street is The Benedum Center for the Performing Arts, where performances for the Civic Light Opera, The Pittsburgh Ballet Theater, and the Pittsburgh Opera occur. While you are in the area, keep your eye out for the August Wilson Center for African American Culture.

Liberty Avenue runs parallel to Penn Avenue, and at 980 Liberty Avenue is the theater that was named for August Wilson, a native Pittsburgher, Pulitzer Prize winner, and Tony Award winning playwright. At 945 Liberty Avenue is The ToonSeum, which is dedicated to the cartoon arts. It is only one of three museums like it in the United States.

You will begin to notice that Pittsburgh’s connection to Heinz is thicker than its ketchup. Pittsburgh has Heinz Hall, Heinz Field, Heinz Chapel, Heinz Swamp (just kidding on that one) and The Heinz History Center.

Our favorite spot here is the “eye ball” benches at the Agnes R. Katz Plaza where Penn and Seventh intersect. Ask a passerby to take your picture on one. You will be certainly a “sight”!

Trivia:

The O’Reilly Theatre has a Heinz connection too. What is its link to the ketchup empire? 

 

Continue walking up Penn Avenue, passing the David L. Lawrence Convention Center on your left. Cross over 11th Street, turn left and walk a block until you hit Smallman Street. Turn right onto Smallman Street and head past the Senator John Heinz Regional History Center. You will enter the Strip District.

 

3. The Strip District

This is one of Pittsburgh’s most colorful and vibrant areas. It’s where urban and chic collide as well as upscale and gritty. Here you’ll find fish mongers and fine dining, Pittsburgh memorabilia and Primanti sandwiches, nightlife and loft-living. We recommend just wandering in and out of the stores and sampling the food. Pick up a Terrible Towel while you are here and maybe a biscotti or two.

There’s a ton of great photo opportunities here, though we think nothing beats posing with the fish at Wholey’s (1711 Penn Avenue). Posing is better than sleeping with the fish, right?

Trivia:

Since the 1950s, this company in The Strip has claimed the title of “The Party King.” Who is Pittsburgh’s “party king”? 

 

From Penn Avenue, find one of the cross streets and head toward Liberty Avenue. Once at Liberty, turn right and head back into town. On your way back into the heart of the city, you will come to the Pennsylvanian.

 

4. The Pennsylvanian

If a building could talk, this one on the left located at 1100 Liberty Avenue would certainly have a tale to tell. When railroads were king, anyone who came to Pittsburgh by train passed through this jewel of a building, which was formerly known as Penn Station. Alexander Cassatt, the brother of famed painter Mary Cassatt, was the President of the Pennsylvania Railroad in the early 20th Century. He commissioned this train station. Daniel Burnham, the noted architect and man behind the World’s Columbian Exposition, or as it’s better known, the Chicago World’s Fair, designed this beautiful building that features a domed rotunda. Today, the building is known as The Pennsylvanian and is an apartment building. Located in a smaller area of a lower level is Pittsburgh’s Amtrak train station.

Trivia:

Burnham was the architect of the Chicago World’s Fair, but that exposition has another Pittsburgh connection. The WHEELS were turning in his mind when this Pittsburgher invented a unique structure that made its debut at the Chicago World’s Fair.

 

From the Pennsylvanian, you will soon come to the junction of Liberty Avenue and Grant Street. Head left onto Grant Street, and shortly you will arrive at the US Steel Tower.

 

5. The U. S. Steel Tower

U.S. Steel BuildingThis is the house that steel built. In 1970, U.S. Steel Corp opened this 70-story building at 600 Grant Street as its headquarters, calling it the U.S. Steel Building. Although no longer the owner of the building, U. S. Steel is still one of the largest tenants occupying it. UPMC now has its headquarters in the building, hence the UPMC logo atop the building. During the holiday season, The Pittsburgh Creche is located in the surrounding Steel Plaza and attracts thousands of visitors to view this amazing and unique display.

Trivia:

The Steel Building has undergone several name changes over the decades. With a recent name change, it lost a letter. Which of Mr. Rogers’ feathered friends is speculated to have taken it?

 

Proceed along Grant Street for several blocks until you come to 436 Grant Street on the left, which is the Courthouse.

 

6. The Allegheny County Courthouse & Jail

Allegheny County CourthouseThis imposing building and jailhouse was designed by noted Boston architect Henry Hobson Richardson. It was the location for a scandal that was eventually featured on the silver screen. Mrs. Soffel, the 1984 movie that starred Mel Gibson and Diane Keaton, relates the early 20th Century escape from this jail by the Biddle Brothers, who were aided by the warden’s wife, Kate Soffel. The jail officially closed in 1995. The complex is bordered by streets named for the city’s founding fathers: John Forbes (Forbes Ave), James Grant (Grant Street), and James Ross (Ross Street).

Trivia:

What is  Allegheny County Courthouse and Jail’s CONNECTION with Venice?

 

Go back to Grant Street and head further down to 436 Grant Street, to the City-County Building.

 

7. The City-County Building

This building is the seat of government for the city of Pittsburgh, and it also houses Allegheny County and Pittsburgh government offices. Outside the building is the statue of Mayor Richard Caliguiri, who served as the city’s mayor from 1977 until his death in 1988. Also, the steps of the building have featured in many movies.

Trivia:

Mayor Caliguiri died from a rare disease, Amyloidosis. Only 12 years later another CASE of Amyloidosis was diagnosed in another prominent politician that took his life. Who was the other politician?

 

Walk back up Grant Street in the direction from which you came until you come to Fifth Avenue. Turn left onto Fifth Avenue and walk until you come to Smithfield Street. At the corner of Fifth Avenue and Smithfield Street, look up, and you will find the Kaufmann’s Clock, one of Pittsburgh’s most beloved landmarks.

 

8. Kaufmann’s Clock

Kaufmann’s ClockIn 2013, this clock celebrated 100 years of presiding over this corner. The site of the former Kaufmann’s Department Store, the building is under construction for future apartments, but for decades, people coming to town would use the venerable landmark as a meeting place, hence the phrase “Meet you under the Kaufmann’s clock.”

Trivia:

It may sound CORNY but when the clock was refurbished in 1987, there was so much dirt and grime, nothing the specialists used seemed to work. At last, 1,000 pounds of what material was used to finally clean it?

 

From under the clock, cross Fifth Avenue and continue down Smithfield Street until you arrive at Sixth Avenue. Turn left onto Sixth Avenue where you will find William Penn’s Land.

 

9. William Penn’s Land

William Penn's LandThis part of the city originally came from land grants from the family of William Penn, who founded Pennsylvania. On this street, you will find two of the city’s most interesting churches: Trinity Cathedral and First Presbyterian Church of Pittsburgh. In 1787, this land, which had been used as a burial ground by the Native Americans, the French from Fort Duquesne, and the British from Fort Pitt, was given to representatives of the Episcopal and Presbyterian churches. At 328 Sixth Avenue is Trinity Cathedral, and at 320 is the First Presbyterian Church of Pittsburgh. Trinity Cathedral was where Pittsburgh composer Stephen Foster worshipped. In the churchyard between the two houses of worship lies the burial ground. It is estimated that 4,000 people were buried in this plot of land. Among the many notable people laid to rest there are Red Pole, the Shawnee nation chief, and Dr. Nathaniel Bedford, the city’s first doctor and founder of the University of Pittsburgh.

Question:

Thirteen of the 14 stained-glass windows in the sanctuary of First Presbyterian Church were designed and installed by a famous artist who shares a name with which 80’s pop singer, and we don’t mean Debbie Gibson.

 

Proceed down Sixth Avenue to Wood Street. Turn left onto Wood and walk three blocks until you arrive at Forbes Avenue. Turn right onto Forbes and continue until you come to Market Square.

 

10. Market Square

What piazzas are to Italians and plazas to the Spanish, Market Square is to Pittsburgh. Since the late 1700’s, this open space in the city has been a hub. It has received more makeovers during the decades than a Hollywood star, but today, it is home to historic restaurants and new ones as well. It is a great place to hang out or grab a bite to eat after all of this walking. The Original Oyster House, at 20 Market Square, has been in operation since 1870 and is the oldest bar and restaurant in Pittsburgh. Pittsburghers love fish sandwiches, and this is where that love affair began.

Question:

We’re not trying to MILK these questions, but when eating at the Original Oyster House, what traditional beverage was first served as an alternative to alcohol during Prohibition?

 

Return to Forbes Avenue and continue out of Market Square until you come to Stanwix Street. Cross Stanwix and turn left onto Liberty Avenue. Walk past Gateway Center, and at some point, cross Liberty Avenue onto Commonwealth Place and the entrance to Point State Park.

If you started the tour at No. 1, The Point, this concludes the tour (but feel free to take the loop again).

 

Answers:

  1. The Blockhouse
  2. Anthony O’Reilly, for whom the theater is named, was once the CEO and Chairman of the H. J. Heinz Company
  3. Mike Feinberg Company
  4. The Ferris Wheel, constructed by Pittsburgh engineer, George Ferris.
  5. The building’s name was changed in 1988 to the USX Tower to reflect U.S. Steel’s new corporate identity. In 2002, it was renamed, once again, to the U.S. Steel Tower. There is no truth to the rumor that X, Mr. Rogers’ friend the Owl, took the letter and is hiding it in his oak tree.
  6. The courthouse is connected to the jail by the Bridge of Sighs, which was modeled after the one in Venice that connected the Doge’s interrogation rooms to the prison. Both enclosed bridges have windows that afforded prisoners their last glimpse of freedom. They were said to “sigh” at their loss.
  7. Pennsylvania Governor Robert Casey died in 2000 from Amyloidosis too.
  8. Ground corncobs were blasted under high pressure to clean it.
  9. Tiffany
  10. Buttermilk