Pittsburgh and Its Countryside South
PA 101
Western PA's Greatest Hits
Duration: Two days and two nights
There aren’t many places where you can get a complete education that covers art, natural science and history like you can in the Pittsburgh area. This road trip will give you a lesson on two of the most renowned artists of our time in Andy Warhol and Frank Lloyd Wright. You will also learn the importance of economics during our shopping excursions. Nature will be front and center as you scale Mount Washington and visit one of Western Pennsylvania’s beautiful state parks. And, through it all, you will come face-to-face with history at every turn. Buckle up and hit the road with us as we explore all that greater Pittsburgh and Western Pennsylvania has to offer.
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Mount Washington / Duquesne Incline
Start your day with a trip to the top of Mount Washington for the most spectacular view of downtown Pittsburgh. Seriously, we’re talking birds eye view here, so be sure to bring your camera along for what is sure to be some incredible photo opportunities. And, the best way to get to the top of Mount Washington? That’s easy, the Duquesne Incline. You’ll enjoy a peaceful and enjoyable ride to the top in the incline cable car, and once at the top be sure to check out Pittsburgh’s famous Restaurant Row and other great attractions.
Warhol Museum (North Side)
Once you’ve made your way down from atop Mount Washington, your next stop will be the Andy Warhol Museum located across the river. If the weather is nice, it’s an easy walk over to the North Shore where the museum is located. Here you will discover the largest museum in the United Stated devoted to a single artist. On display are paintings, photographs, prints and sculptures created by the Pittsburgh-born pop art icon. Take your time…there’s a lot to see and digest here.
Tour Nationality Rooms at the Cathedral of Learning (University of Pittsburgh in Oakland)
Next on our tour—and in keeping with our theme of learning—is the Cathedral of Learning on the campus of the University of Pittsburgh. The Cathedral of Learning was formally opened in 1937 and is the second tallest university building in the world. Listed on the National Register of Historic Places, the 42-story building houses classrooms, theaters, laboratories and departmental offices. Spend some time in the lobby, a three-story Gothic room, with some amazing architectural features…but keep in mind, it’s a study area so do try to keep your awe in check.
Shadyside Shops & Galleries (Walnut & Ellsworth Streets)
After a day of scaling Mount Washington, getting your fill of Andy Warhol and visiting the Cathedral of Learning, there’s no better way to unwind than with a visit to the Shadyside section of the city. In this quiet area—named for a 19th century railroad station and for its shady street and pathways—you’ll find a wealth of quaint shops and boutiques, as well as a nice mix of higher end stores. Take some time to walk up and down these historic streets and enjoy the great shopping and dining this area offers.
Eat Here
Lidia's Italy (Pittsburgh)
Owned and operated by television chef Lidia Bastianich and her son Joseph, this restaurant serves up some of the best traditional and contemporary Italian fare you will find anywhere.
Sleep Here
Omni William Penn (Downtown Pittsburgh)
Charming. Elegant. Luxurious. Just a few words used to describe this classic hotel that has been home away from home for visitors to Pittsburgh since 1916.
Check out these ready-to-ride roadtrips for similar destinations
Civil War Trails
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Spree - The Shoppers Roadtrip
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Fallingwater (Mill Run)
Day 2 begins with a trip to one of the more amazing architectural structures in the area: Fallingwater. Designed by Frank Lloyd Wright in 1935, this magnificent structure will leave you awestruck as you admire both its beauty and functionality. Partially built over a waterfall along the Bear Run River, Fallingwater, which is listed on the National Register of Historic Places and is a National Landmark, has been hailed as Wright’s most beautiful creation and once you visit you will certainly agree. Prepare yourself for a place where nature and human ingenuity meet in a wonderful marriage of awe-inspiring scenic beauty.
Ohiopyle State Park (Ohiopyle)
In keeping with nature theme, your next stop for the day is Ohiopyle State Park. With more than 19,000 acres, this state park is a great place to appreciate the natural beauty of Western Pennsylvania. If you’re really adventurous—and the weather is cooperating—you might want to take a whitewater boat ride along the 14 miles of the Youghiogheny River that winds through the park. These rapids are among the best in the Eastern U.S. and are sure to get your heart pumping with excitement.
Southside Works (Southside)
Finally, let’s return to the city for a round of shopping at Southside Works. This open-air entertainment, retail and residential complex is located on the South Side (thus the name) and covers more than 34 acres. Here you will find a perfect mix of high end and moderately priced boutiques, as well as some great options for dining and entertainment. It’s the perfect way to end your road trip.
Eat Here
Hofbråuhaus (Pittsburgh)
If you enjoy great German cuisine served with outstanding German beer in a lively, festive setting modeled after a Bavarian beer hall, then this is the perfect place for you.
Sleep Here
Omni William Penn (Downtown Pittsburgh)
We knew you'd love this hotel. Since you're coming back to Pittsburgh, stay here both nights.
Check out these ready-to-ride roadtrips for similar destinations
Civil War Trails
Artisian Ways
Spree - The Shoppers Roadtrip
Fairway Drive
Trails Mix
Shunpiker's Guide
Ghost Rides



