I've been fortunate enough to live in and visit many interesting places around the globe. My time in the US Navy, coupled with my love of travel has taken me to dozens of unforgettable destinations. When visiting a new city, I always try to do and see things that can only be done there. I eat at local restaurants instead of national chains, shop at stores that I don't have at home, and spend time in places and destinations unique to that place. From conversations with our guests over the years, I've learned that a lot of travelers have this mindset. I'm often asked for recommendations on what I would do in Pittsburgh if I were only here for a few days. Although my answer could change depending on the day and my mood, you can't go wrong with these suggestions for a great fall weekend in Pittsburgh. You could also checkout this site for some other great Pittsburgh destinations.
Morning: Breakfast at Pamela's Diner in Shadyside.
Early Afternoon: Hang out on Walnut Street for shopping or have a walk around Shadyside to check out the unique houses.
Afternoon: Take a quick drive down 5th Avenue to Oakland, the home of CMU and Pitt (be sure to tour the Cathedral of Learning, the tallest university building in the US…it’s pretty amazing).
Early Evening: Park the car and take a short walk or Uber over to Ellsworth Avenue in Shadyside for some pre-dinner drinks (happy hour is from 5 to 7 at Soba).
Evening: Take a 5 minute Uber to Lawrenceville for dinner on Butler Street. Lots of great options there.
Late Evening: Cap the night off with a bar crawl on Butler Street in Lawrenceville.
Day 1 Recap – Neighborhoods visited: Shadyside, Oakland, Lawrenceville
Morning: Breakfast at Pointe Brugge in Point Breeze (be sure to make reservations ahead of time)
Early Afternoon: Stick around Point Breeze and tour The Frick. It’s Henry Clay Frick’s estate and there's a lot to see including the Frick garage, a large collection of antique cars and carriages.
Afternoon: Head over to the Strip District for a very unique shopping experience (parking can be tough in the Strip. It may be worth an Uber).
Early Evening: Continue to Market Square downtown for some sight seeing. It might also be worth having a walk through Point State Park if the weather permits.
Evening: Make your way to Penn Avenue downtown for dinner. Plenty of amazing restaurants in that area (reservations are recommended).
Late Evening: Stick around Penn Avenue for a live show, dancing, or drinks.
Day 2 Recap – Neighborhoods visited: Point Breeze, Strip District, Downtown
Morning: Enjoy a nice brunch at Grand Concourse restaurant in Station Square.
Early Afternoon: Take a Gateway Clipper ride along the three rivers over to the North Shore (call in advance to reserve your ticket).
Afternoon: Check out a Steelers game or just hang out at one of the many restaurants and bars the North Shore has to offer.
Early Evening: Catch the return Gateway Clipper boat back to Station Square and ride the Monogohela Incline up to Grand View Avenue in Mount Washington. Both a must when visiting Pittsburgh.
Evening: Have dinner at one of the many fine restaurants along the Grand View Avenue cliffside and enjoy the amazing city views at sunset (reservations are a must).
Late Evening: Ride the incline back down to Station Square and wind down the night in Bessemer Court.
Recap – Neighborhoods visited: Station Square, North Shore, Mount Washington