
Historic hotels of Pittsburgh have interesting beginnings and fascinating histories. Many of the hotels had previous lives before they housed visitors. One was a Benedictine monastery and another was a private home.
The Priory Hotel, located on Pressley Street in the historic Deutschtown section of Pittsburgh’s North Side, is appropriately named. Built in 1854 as The St. Mary’s Priory, the building was home to Benedictine monks and priests. The Grand Hall, the banquet facility of The Priory, was St. Mary’s Church. According to John Graf, president and CEO of The Priory Hospitality Group and one of the owners of the hotel, St. Mary’s was an active parish until the 1970s when PennDOT purchased the buildings to make way for the construction of I-279, despite its historical significance. With a bleak future, the priory and church dwindled in size until the last mass was held in 1981. Fortunately, despite the death sentence for the buildings, it wasn’t the end. Graf said that St. Boniface, a nearby Catholic Church, was also slated to be demolished, but the vocal community convinced PennDOT to reroute the new highway. Both churches and the priory were saved.
Graf’s parents, Edward and Mary Ann, purchased The Priory and St. Mary’s Church from PennDOT in an auction in 1984. “My parents were very interested in historical buildings, but at the time, they weren’t sure what they were going to do with them,” Graf said. A friend encouraged the couple to turn The Priory into a boutique, European-style hotel, citing that the nearby hospitals would serve as a good source for guests. In 1986, The Priory Hotel opened with 25 guest rooms. In 2011, the Grafs added 17 more rooms, and in 2022, they took advantage of closures from COVID to renovate the hotel once again. The Grand Hall, the former St. Mary’s Church, took a bit longer to renovate due to parking limitations, Graf explained. The Hall was opened in 1995 with many of the original features including restored stained glass windows and the baptismal font. Graf’s wife, Suzanne, helps to manage the Grand Hall.
The Priory’s 170-year-old history is an integral part of the experience. “We are an authentic part of our historic neighborhood. This is something that can’t be recreated,” Graf said.
The Omni William Penn Hotel was one of the largest and most ornate hotels of its time. Located in the heart of downtown Pittsburgh, it still has the beauty, grandeur, and status today. Commissioned by Pittsburgh icon Henry Clay Frick, the William Penn opened in 1916 at a cost of six million dollars with 1000 guest rooms and a two-tiered grand ballroom. At the time, it was the largest hotel from Pittsburgh to Chicago according to Bob Page, area director of sales and marketing for the Omni William Penn Hotel. “There are many firsts for the hotel. It was one of the first to have electric lighting and iced drinking water on tap. Each room had its own private bath – very rare in those days. It is all attributed to Frick because he wanted the best of everything,” Page said.
The ornate hotel was considered “the most modern hotel of its time” according to hotel history. “There was every imaginable service that you needed available at the hotel – a bakery, a silversmith, a barber shop, and a candlestick maker. It was said that you could live there and never have to leave the hotel,” Page said. Single rooms were $2.50 and the most expensive suite, where Henry Clay Frick stayed opening night, was $50 at the time. In 1929, the Grant St. Annex was added with an additional 600 rooms.
Over the decades, like most hotels, the William Penn faced many financial challenges. There were also numerous renovations and upgrades. And of course, numerous historical figures have visited or stayed, including Bob Hope and every seated president since Theodore Roosevelt (except Donald Trump), plus numerous others. The G20 Summit in 2009 was also hosted at the William Penn.
A fun historical note: Lawrence Welk played at the William Penn 1939 New Year’s Eve celebration, and his original bubble machine was created by a hotel worker. The hotel still houses the machine, bringing it out for special occasions, Page said.
Today, the hotel houses 597 guest rooms with six different food and beverage experience opportunities, including the historical Speakeasy, an authentic 1920s speakeasy that was restored to its original beauty. “It is a place of history itself. I love to show visitors the old whiskey bottles and other original items,” Page said. Much of the hotel’s history is displayed in the Heritage Hall of the hotel where visitors are welcome to peruse at their leisure.

The Omni William Penn is a member of Historic Hotels of America, the official program of the National Trust for Historic Preservation that recognizes and celebrates historic hotels.
The Mansions on Fifth, located on “Millionaires’ Row” on Shadyside’s Fifth Avenue, was built as two separate houses by Willis F. McCook. The larger 20,000 square foot mansion was built as a home for McCook, his wife, Mary, and their 10 children in 1906. At the same time, McCook’s daughter, Bessie, became engaged and he built her an 8,000 square foot home a mere 15 feet behind the larger mansion. The total project cost $300,000 and featured decorative ironwork, leaded and stained glass installations, and decorative tile along with beautiful carved woodwork. The Mansions on Fifth are also owned by the Priory Hospitality Group and overseen by John Graf.
As the years passed, the McCook family didn’t have the means to maintain the property and lost it in the 1930s. Emil and Margaret Benavita Jr. purchased the larger mansion in a sheriff’s sale for $28,000 in 1949. Bessie McCook Reed lived in her home until her death in 1966, at which time the Benavitas also attained that property. The Benavitas ran the larger mansion as a boarding house for college students until a fire gutted the mansion in 2004. After, it was sold and restored by Mary Del Brady and Richard Pearson who operated the mansions as guest rooms, meeting spaces, and the Oak Room Pub. The properties were recognized as historic landmarks by the National Trust for Historic Preservation in 2012.
The Priory Group acquired operating assets of the two properties in 2016. “What’s really cool about these properties is that many of the other millionaires’ homes have been torn down or turned into condos. Some are private homes. Ours are pretty much the only ones that you can walk into and enjoy many of the historical features,” Graf said. “Many of the stained glass windows, the original fireplace of the ground floor of the mansion, and the woodwork are the same today as they were in 1910.”
Mansions on Fifth serves as a boutique hotel with 13 guest rooms in the Fifth Avenue House and an additional nine rooms in the Amberson House.
For more information:
The Priory Hotel:
866-3PRIORY. For information
on The Grand Hall visit:
or phone 412-323-9394.
Omni William Penn Hotel:
phone 412-281-7100.
The Mansions on Fifth:
412-381-5105.
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