Voted one of the best tours of Pittsburgh by Pittsburgh Magazine.


About the City Tour:

For those looking for to explore a little more of Pittsburgh, there is the Highmark City Tour. Starting at the Southside Riverfront Park, this ride offers 25 miles of fun on lower-traffic streets, as you sightsee throughout Pittsburgh’s South Side, Northside, and East End. Expect a few mild hills. With rest stops placed strategically throughout this route, even unexperienced riders can enjoy this ride at their own pace.  Join REI for the official finish line festival when you get back to Pittsburgh’s historic Southside. Everyone is welcome to stay and enjoy the day. At the Finish Line Festival there will be restrooms, bike parking (don’t forget to bring your bike lock), music, food trucks, a cycling expo. It’s going to be fun!

Start time: 9:00 AM

For details on the route and GPS files, click here.


  • Pittsburgh’s Historic South Side
  • Downtown
  • Northside
  • Strip District
  • Bloomfield
  • East Liberty
  • Highland Park
  • Larimer
  • Point Breeze
  • Squirrel Hill
  • Oakland
  • Uptown

Rest Stops:

Water Stop @ Allegheny Square – Mile 5

Highmark’s Highland Park Rest Stop- Mile 14 Enjoy snacks and refreshments by Giant Eagle

Rest Stop at Schenley Park – Mile 21 Enjoy snacks and refreshments by Giant Eagle

Ride profile: