Highmark City Tour 25 Miles


About the Ride

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 REI Finish Line Festival there will be restrooms, bike parking (don’t forget to bring your bike lock), music, food trucks, a cycling expo, and a free photo booth. It’s going to be fun!

Start time: 8:00AM-8:30AM 
We recommend  starting early to enjoy lighter traffic on the streets as well as to beat the heat.

(If you’re planning to take the ’45-mile Option’, start time will be 7:30-8:00am)


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

Rest Stops:

Water Stop @ Allegheny Square – Mile 5

Highmark’s Highland Park Rest Stop- Mile 14 Enjoy snacks and refreshments by Whole Foods Pittsburgh

Eat’n Park Rest Stop at Schenley Park – Mile 21 Enjoy snacks and refreshments by Whole Foods Pittsburgh


Ride profile


Register for the Highmark City Tour