City Cast

Gear Up for Pittsburgh's Best Biking Events

Francesca Dabecco
Francesca Dabecco
Posted on July 24
A cyclist riding over the bridge

A cyclist riding over the bridge. (Francesca Dabecco / City Cast Pittsburgh)

There are some things you need to know before you start biking in Pittsburgh, like rules of the road, how to keep yourself safe, and how to trek up our city’s hills on an e-bike.

Then there’s all of the fun stuff, like races, trails, and cycling groups. Last year, we talked to Monica Garrison, founder of Black Girls Do Bike, about some of her favorite cycling events in Pittsburgh:

“I think it is pretty cool that folks are that free and not worried about the outside world. They just hop on their bikes and ride through Downtown.”

  • Gear up: The Underwear Ride is happening this Thursday, July 27 at 8 p.m., starting at World War I Memorial Park in Lawrenceville.

“I think Pedal Pittsburgh is probably my favorite ride just because you can pick where you’re comfortable at riding, and it brings out pretty much the whole cycling community.”

  • Gear up: Choose from the 10-mile, 25-mile, 40-mile, or 62-mile trek at Pennsylvania’s largest bike ride on Aug. 27 at Southside Riverfront Park. Tickets are $5-$190 (depending on which swag package you choose) and there’s only a week left to register at a discounted price. Proceeds support BikePGH.

“That’s on the 12 highest elevated streets in Pittsburgh, and several riders attempt to conquer them one after another on the same day. I don’t do that ride, but I admire anyone who puts their hat in the ring to try it.”

  • Gear up: The 40th annual ride is on Saturday, Oct. 28 and starts at Rhododendron Shelter in Highland Park. Register for a discounted fee before Oct. 20 at

“It’s an awesome ride where women of all ages come together. What’s great about this ride is that it’s in February, so it’s always cold, and they kill it every year.”

  • Gear up: Pittsburgh Babes on Bikes hasn’t announced a 2023 date yet, but read about the spouses who co-directed a documentary on it called “A Bitch of a Race.”
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