My partner and I are both longtime metro Detroiters whose roots are in the Laurel Highlands of PA.
We still have plenty of family and reunions in Somerset county PA. We're both members of the Western Pennsylvania Conservancy and have a great interest in Fallingwater, Ohiopyle and Kentuck Knob. We both recommend a visit to nearby Kentuck Knob which can be described as a more modest "small" design compared to the more ambitious Fallingwater. Kentuck Knob was originally known as the Hagan House when I was youngster in Meyersdale & Salisbury eating Hagan ice cream.
My partner's interior design career enabled us to spend half day visits in and out of the Fallingwater home and site. Watching the amount of work needed to restore and maintain it has been mind boggling. I've loved every minute I've spent there and cost has not been a concern to us at all. Rafting the Youghiogheny at Ohiopyle is fun as well as biking the Great Allegheny Passage. Near my hometown the Passage crosses over the Salisbury Viaduct, a wonderful reuse of a huge Western Maryland RR trestle bridge. It's really a thrill as is going through the old railroad tunnels as the trail crosses into MD from PA.
When it's in operation a ride on the Western Maryland railroad's steam locomotive train between Cumberland and Frostburg MD has some good scenery and Frostburg is a great university town with a unique Main street. I also have relatives in Grantsville, Frostburg, LaVale and Cumberland.
We always enjoy time on the old National Pike including a visit to the Penn Alps restaurant (although it's not as authentically local foods as it has been in the past). We used to find dried corn and smoked sausage there just like Grandma used to make. Adjoining the restaurant in the forest are seasonal art and crafts booths. The Stonehouse restaurant is reliable and we always enjoy a stay at the Historic Summit Inn with it's mission style design (Henry Ford stayed there 90 years ago). Sadly the Casselman Bridge near Grantsville MD is undergoing repair but it's the first bridge funded by the new US government, signed by James Madison.
Pittsburgh's got many attractions - bird enthusiasts should enjoy the National Aviary and the Pittsburgh Zoo makes great use of the unique terrain. We like staying with our friends near Kennywood amusement park for some rides on it's historic roller coasters. The city's 2 incline trolleys are interesting experiences.
That's just off the top of my head - it's really a colorful historic region. My partner's roots are in Johnstown and Nanty Glo - there's an incline trolley in Johnstown but it may be under repair - not sure about it.
I've got an emotional connection to the stretch of PA turnpike from Somerset to Ohio as my family traveled it hundreds of times - it was engineered for a train and feels like a wild mouse ride at times. It just made me think of visiting Fort Ligonier again - a favorite school 4th grade field trip! We'd take the Donegal exit off the turnpike and drive north to Route 30.