Pittsburgh’s Oakland neighborhood is the education center of the city. Each year thousands of students move into this area to attend one of the universities located there. Being a newcomer, or even a resident who hasn’t ventured to this area of the city recently, can be a bit overwhelming and disorienting.

At Popular Pittsburgh we know how that feels. A few years ago, my husband and I went to Rome. Our hotel was located within blocks of the Vatican. Although the official tour did not begin until the next day, we couldn’t resist taking a look around St. Peter’s Basilica on our own. The next day during the official tour, our guide led us into the massive church and began noting points of interest. She then pointed to the right and said, “As you can tell from the crowds, there is Michelangelo’s masterpiece The Pieta.” My husband and I looked at each other dumbfounded. The night before, we had walked right past The Pieta without ever realizing it.

Oakland can be a bit like The Pieta. There are gems found throughout this area east of downtown Pittsburgh, but if you don’t know what you are looking for, you may just pass one up. And the beauty of Oakland is that there is something of interest for everyone. From historical to sports sites to spiritual centers, Oakland is packed tighter with points of interest than a pincushion.

Popular Pittsburgh wants to help you get the most of your time in Oakland and have a bit of fun while you explore this part of the city. Therefore, we created our Tour of Oakland. Unlike a traditional scavenger hunt where you collect items from the various points of interest along the way, we’re suggesting that you take selfies. Sure, we could have had you collect a napkin from the Original Hot Dog Shop or a church bulletin from St. Paul Cathedral, but we knew you’d eventually throw them away, and besides, with your permission, we’d like to feature your photos on our Instagram and Facebook. And as those smart alecks used to say in grade school, “Take a picture. It lasts longer!”

In addition, we’ve also made the tour a bit of a mystery. For each landmark, we’ve included some information and a question. Each question contains a hint to the answer. Correct answers are posted below.

You can begin the tour at any of the 12 points of interest and pick up the hunt from there by going to the following site. Along the way, feel free to take in the other venues. Many of the sites highlighted on the tour require extra time to fully explore them. Forbes and Fifth Avenue are the two main thoroughfares in this area, with most of the attractions located near one of these streets. Also, the Cathedral of Learning is a great way to orient yourself. This tower can be seen from most any location.  If you get lost, head to the cathedral or just ask someone for directions to one of these streets and you will be fine. 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 and whether you explore in more depth some of the sites along the way. It should take a few hours, but there is no reason to rush. Enjoy Oakland and don’t forget to tag your photos with #popularpittsburgh.

1. The Cathedral of Learning

The Cathedral of Learning, Pittsburgh PAThe University of Pittsburgh’s most identifiable building, The Cathedral of Learning, is the second tallest educational building in the world, only dwarfed by The University of Moscow’s main building.  Located at 4200 Fifth Avenue, the Cathedral of Learning stands 535 feet tall with 42 floors.  The building houses the famed Nationality Rooms on the lower floors.  If the Nationality Rooms are open, wander about and be amazed at these working classrooms.  If they are not open, the cathedral is still impressive and looks like a school building where Harry Potter may have attended classes.

Question:  In addition to the Nationality Rooms, the Cathedral of Learning is home to some of these.  Although their name may suggest it, they do not hail from Atlanta.

*******If you go inside the cathedral, take a photo in front of one of the Nationality Rooms.  If you choose to remain outside, there are limitless vantage points where you can capture a shot with this iconic building.

The cathedral is situated nearly in the center of a distorted rectangle, bordered by Fifth Avenue to the north, Bigelow Boulevard to the west, Forbes Avenue to the South, and S. Bellefield Street to the east.  Head east on the pathways toward S. Bellefield Street, and you will soon find a smaller, gothic style building, which is:

2. Heinz Memorial Chapel

This non-denominational chapel was a gift to the University of Pittsburgh from H. J. Heinz as a way to heinzchapelhonor his mother, Anna Margaretta Heinz.  It was dedicated in 1938.  Of the many events held every year at the chapel, among them are nearly 200 weddings.  To be married at Heinz Chapel, you must be affiliated with the University of Pittsburgh or be employed by Heinz Corp.

Question:  All of the stained glass windows were created by one man, Charles Connick, which is usually not the case.  You’d be “pressed” to find a stained glass artist with stronger ties to Pittsburgh than Connick as he was once on staff of this defunct Pittsburgh newspaper.

*******Like the cathedral there are numerous views for photographing this lovely gift from the Heinz family.

On S. Bellefield, turn left and head toward Fifth Avenue.  When you reach Fifth Avenue, turn right and walk until you come to S. Dithridge Street.  Cross Fifth Avenue and at 108 N. Dithridge Street, you will find another iconic house of worship:

3. St. Paul Cathedral

The cathedral is the seat of the Roman Catholic diocese of Pittsburgh and its more than 750,000 Catholics.  The Gothic style cathedralst-pauls-cathedral was built in 1906.  At that time, many Pittsburghers had moved from downtown Pittsburgh, which was becoming an industrial center, to suburban Oakland.  The diocese decided to move the cathedral too from downtown Pittsburgh to Oakland.

Question:  Many questioned the bishop at that time for selecting Oakland for the cathedral.  What was the name of that bishop?  I have a good “feelin” you might know the answer.

*******Take a photo on the steps of St. Paul Cathedral.

From St. Paul Cathedral head west toward the direction of the Cathedral of Learning, until you come to 4141 Fifth Avenue and:

4. Soldiers & Sailors Memorial Hall

The nation’s only military museum dedicated to those who served in any branch of the service, Soldiers & Sailors was originally builtsoldiersandsailors to honor the Civil War veterans of Allegheny County.  Today, it honors all those who have served the nation from Pennsylvania.  Dedicated in 1910, Soldiers & Sailors is situated on an expansive lawn dotted with canons and other military apparatus, and it houses war artifacts and unique exhibits from the Civil War until today’s conflicts.

Question:  It’s hard to “keep quiet” about this creepy movie that was filmed here and had people “flocking” to the movies.

*******Pose with one of the many military artifacts on the lawn.  Who can resist a photo with a torpedo?

From Soldiers & Sailors continue west on Fifth Avenue, passing the William Pitt Union across the street on your left, at 4200 Fifth Avenue.  Formerly the Hotel Schenley, it is now the student union for the University of Pittsburgh.  On your right at 4215 Fifth Avenue is The Pittsburgh Athletic Association, the private social and athletic club opened in 1908.  The stately building has a pool on the third floor and a 16-lane bowling alley within.  Both the PAA and the Hotel Schenley were works of real estate developer Franklin Nicola.  Walk past several university halls until you come to DeSoto Street.  Turn right and walk up the hill.  At the top continue to the left as it turns into Terrace Street and you will come to:

5. The Peterson Events Center & Salk Hall

This arena is where the University of Pittsburgh plays basketball.  It opened in 2002 on the The Peterson Events Center and Salk Hallformer site of Pitt Stadium.  Continue past The Peterson Events Center to Salk Hall at 3501 Terrace Street.  There on the lawn is a historical marker commemorating the site where noted medical researcher Jonas Salk conducted research on the first polio vaccine.

Question:  For Pete’s sake you better get this answer.  What is the nickname of the Peterson events center?

*******Take a photo next to the plaque honoring Jonas Salk’s work.  Then take one at The Peterson Events Center.

Continue along Terrace Street until you arrive at Lothrop Street.  Turn left onto Lothrop and walk down the hill until you come once again to Fifth Avenue.  At Fifth, turn right and walk past the numerous buildings that make up the UPMC medical complex.  Continue on and you will arrive at the campus buildings of Carlow University.  At Halket Street, turn left and proceed on Halket until you come to the other major street in Oakland, Forbes Avenue.  At Forbes turn left and enter the heart of Oakland’s business district.  There are numerous places to eat along this thoroughfare including:

6. The Original Hot Dog Shop

The “O,” as it is commonly known, opened in 1960, and it’s just not a visit to Oakland unless The Original Hot Dog Shopyou’ve stopped in for a bite to eat at this neighborhood fixture.

Question:  Frankly speaking, The Original Hot Dog Shop was not the “O’s” original name.  What was its first name?

*******This is a no-brainer.  Take a photo of yourself digging into a dog or a heaping plate of “O” fries.

Continue down Forbes Avenue past the many University of Pittsburgh Halls until you arrive at Schenley Drive.  Cross the street and turn right onto Schenley Drive and proceed a block or so until you come to:

7. Forbes Field & The Wall

This area of Oakland is where Forbes Field was once situated.  All that remains of that baseballMazeroski Field & The Wall park is part of the outfield wall and flag pole in their original location.  It was over this wall that Pirate Bill Mazeroski hit his legendary home run to win the 1960 World Series.  To commemorate that occasion, fans visit the wall and the adjacent field named in honor of the second baseman.

Question:  What was the name of the Yankee pitcher who Mazeroski “terrorized” with his World Series blast?

*******Take your photo in front of the outfield wall at one of Pittsburgh’s most historic sports sites.

Walk back the way you came to the corner of Schenley Drive, turn right and follow it across the bridge until you come to the complex of large glass buildings on the right, which is:

8. Phipps Conservatory

Henry Phipps built the conservatory as a gift to the City of Pittsburgh 1893.  Talk about a gift Phipps Conservatory that keeps on giving!  This paradise is home to beautiful gardens and exotic plants and has been a must-visit place for decades.  If you don’t have time to tour it now, be sure to come back when you can properly enjoy Phipps’ wondrous beauty.

Question: You will be “dead” on if you can name the flower that blooms every six to ten years at Phipps and gives off a horrible stench.

*******A good photo spot is one that captures the Victorian greenhouse in the background.  If you go into Phipps, you will find incredible scenes where you can pose for your photo.

If you traveled further on Schenley Drive, you would enter Schenley Park, but this is a vast play land for Pittsburghers, so we recommend scheduling a visit for Schenley Park on another day.  Inside the park there is a golf course, swimming pool, outdoor skating rink, tennis courts, soccer fields, and the Schenley Oval running track.  If you do visit the park, there is a magnificent view of the city and Oakland from the hill atop the Frisbee golf course.

Cross the street from Phipps where you will see Flagstaff Hill.  Locals like to gather here to watch movies in the park.  Head back over the bridge, but not before noting the statue on your left honoring Edward Bigelow, friend of Andrew Carnegie and “Father of City Parks.”  We will talk more about Bigelow when we get to Mary Schenley.  On your left, in front of the Frick Fine Arts Building is:

9. The Mary Schenley Fountain & Schenley Plaza

This fountain and the swath of green space across the street known as Schenley Plaza honor The Mary Schenley Fountain & Schenley PlazaMary Schenley, who donated most of the land in this area.  Mary’s life is one as intriguing as an episode of Downton Abbey.  Mary Croghan Schenley was the granddaughter of pioneering Pittsburgh businessman James O’Hara, and as an only child was the heir to her mother’s considerable land tracts upon her mother’s death.  When she was 15, Mary eloped to England in 1841 with the 43-year-old Captain Schenley.  It was his third elopement and caused scandal all over the country. Her widowed father tried to stop the marriage but was unsuccessful.  But he succeeded in stopping her from inheriting the land.  However the Schenleys fell on hard times and Mary and her father eventually reconciled.  She did visit Pittsburgh from time to time, but remained in England.  In 1889, Edward Bigelow, Pittsburgh’s Director of Public Works, got word that a developer was going to London to convince Mary Schenley to sell him the Mt. Airy Tract.  Bigelow immediately sent a lawyer to England, beating the developer by two days.  Schenley gave the city 300 acres with the option to purchase 120 more, providing that the park Bigelow had in mind be named after her and never be sold.

Across the street from the fountain is Schenley Plaza, which features take-out food kiosks and The Porch restaurant as well as a green space and a spacious garden area with ample seating that invites visitors to sit and chat.  The signature piece in the plaza is the PNC Carousel, where for $1.25 you can take a spin on the merry-go-round.

Question:  It’s no “secret” that Mary Schenley’s romance shocked this English monarch. Which Queen of England refused to receive the Schenleys at court for years?

********A beautiful spot for a photo is with the Schenley Fountain and the Cathedral of Learning in the background.

After exploring the Schenley Fountain and Plaza areas, head toward Schenley Drive extension and walk toward the Cathedral of Learning. When you come to Forbes Avenue, turn right and you will come to:

10. The Carnegie Library, Carnegie Music Hall, Carnegie Museum of Natural History & Carnegie Museum of Art

Andrew CarnegieWhat Schenley was to parks, Andrew Carnegie was to libraries and museums in Pittsburgh.  At 4400 Forbes Avenue is the Carnegie Library, which is the flagship for the 19 other Carnegie branch libraries in the city.  It opened in 1895 and was funded by industrialist Andrew Carnegie.  Carnegie Music Hall hosts lectures and musical entertainment.

Next door, the Carnegie Museum of Natural History has one of the most extensive collection of dinosaur fossils in the world.  The T-Rex will give you nightmares of Jurassic Park proportion.  A day could be spent wandering around these exhibits.  But if you did that, you wouldn’t have time to visit next door at the Carnegie Museum of Art, where you can see masterpieces by artists such as Winslow Homer and James A. McNeill Whistler.

Question:  There are four statues outside the Carnegie of geniuses: Shakespeare, Galileo, and Bach are three of them.  The fourth is the creator of The Pieta, which I referenced at the beginning.

*******Take a photo in front of one of these big guys.

Continue further on Forbes Avenue if you would like to explore the campus of Carnegie Mellon University, which was originally called Carnegie Tech and was founded by you guessed it Andrew Carnegie in 1900.  If your tootsies are tired, cross Forbes at the intersection of Craig Street and head back toward the Cathedral of Learning, passing on your right St. Nicholas Greek Orthodox Cathedral, at 419 S. Dithridge Street, which is the seat of the Greek Orthodox diocese in Pittsburgh.  On Forbes near the lawn of the Cathedral is:

11. The Log Cabin

To celebrate the University of Pittsburgh’s bicentennial in 1987, this log cabin was reconstructed to symbolize Pitt’s beginnings as a frontier academy of higher learning.  The cabin dates to the 1820s/1830s and came from the Yatesboro/Rural Valley area, which is approximately 50 miles from Pittsburgh.  It was reassembled on this lawn.The Log Cabin

Question:  It may be “academic,” but what was the name of the first school that eventually evolved into the University of Pittsburgh?

*******Take a photo with the log cabin and a portion of the Cathedral of Learning to show just how far learning has come in the area.

Located nearby in the shadow of the Cathedral of Learning at 4301 Forbes Avenue is another limestone Gothic style building known as:

12. The Stephen Foster Memorial

Stephen Foster was born in the Lawrenceville neighborhood of Pittsburgh and is known as the The Stephen Foster Memorial“Father of American Music.”  He wrote timeless standards such as Camptown Races, Oh! Susannah, and Beautiful Dreamer that, 150 years later, are still familiar.  At the time he was writing songs, there were no publishing houses, so if he were alive today and earning royalties, he’d be a multi-millionaire.  This memorial is dedicated to him and is also The Center for American Music at the University of Pittsburgh.  It also houses the Stephen Foster Museum which contains exhibits about this composer’s life and his music.

Question:  This “old” song of Stephen Foster’s is played before the start of the Kentucky Derby.

*******The rotunda attached to the main building is quite attractive and makes a good background for a photo.

If you began your tour at No. 1 The Cathedral of Learning, this concludes the tour (unless you’d like to take the loop again.)

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  1. Cathedral of Learning: Peregrine Falcons have been nesting at the top of the cathedral in recent years.
  2. Heinz Chapel: Connick created the windows in his Boston studio, but he was once on the staff of The Pittsburgh Press.
  3. St. Paul: Bishop Richard Phelan was the bishop at the time of the cathedral’s construction.
  4. Soldiers & Sailors: Some scenes from The Silence of the Lambs were filmed at Soldiers & Sailors.
  5. Peterson & Salk: The Pete.
  6. The O: The first name was Original Franks and Burgers.
  7. Forbes Field: Ralph Terry
  8. Phipps: The corpse flower is one of the rarest and largest flowers on earth and smells awful when it blooms.  It last bloomed in August of 2013.
  9. Schenley: Queen Victoria
  10. Carnegie buildings: Michelangelo
  11. Log Cabin: The Pittsburgh Academy is believed to have begun in the 1780s in a log cabin such as this and later became The University of Pittsburgh.
  12. Stephen Foster: My Old Kentucky Home