Shequaya Bailey poses for a portrait

A Major Force

Photo courtesy of Shequaya Bailey

How Shequaya Bailey is growing and diversifying cycling in Pittsburgh.

Movement is what Shequaya Bailey (she/hers) is all about. It’s no surprise that she first got into cycling as a commuter. Bailey still rides to her job as director of operations at Grounded Strategies, which helps communities reclaim vacant land for gardens, playgrounds and other community-led projects. Off the clock, she road bikes, mountain bikes, gravel bikes, and races in the Allegheny Cycling Association series. The ever-jovial rider readily lists exactly what she loves about cycling: “The freedom of movement, to be nimble, the feel of my body making my movement happen, the air, nature.”

And in terms of the cycling community in Pittsburgh, Bailey is not just a mover; she’s a shaker. Her avocation is getting more Black people riding bikes. “It allows people to see what their bodies can do, learn something new either about their city or about biking (and) gain new friendships through those they meet by way of the club,” she says. The club she is referring to is the Pittsburgh Major Taylor Cycling Club, named after Marshall “Major” Taylor (1878-1932), an African-American cycling world champion and world record holder who faced racial discrimination throughout his career. 

To build off that broader legacy, Bailey serves as a member of The Black Foxes, whose manifesto describes the international collective of thought-leading athletes, organizers and influencers as “unapologetically Black cyclists and outdoors-people that are reclaiming our narratives and roles in the outdoors.” And as a self-described “proud, Black, queer, cis woman,” Bailey is an ambassador for Liv Bicycles, a brand of bikes made by and for women. If that’s not enough, she’s also on the board of directors of advocacy nonprofit BikePGH.

Accordingly, her main message to would-be cyclists pushes the simplicity of just starting to ride: It’s not necessary to buy expensive, specialized equipment to begin moving. And if you follow Bailey’s lead at a local event, or on Instagram (@deucedimples), you can capture a little of that positivity in motion—and see it reflected in cycling, fashion and public art content—including her dimples, too.  

Shequaya Bailey poses for a portrait with her bike on a bridge Photo courtesy of Shequaya Bailey

PUBLIC LANDS: What’s your advice for someone just getting into cycling? It can be intimidating.

SHEQUAYA BAILEY: Start where you are. Whatever (bike) you have works for you. It doesn’t make any sense to buy a new bike if you don’t know what kind of rider you’re going to be. Whatever kind of bike you have, go from there. A lot of times people get intimidated by all the things they see other people doing and wearing and riding. As you know, comparison is the thief of joy.

Tell me about the Pittsburgh Major Taylor Cycling Club.

It is a club aimed at encouraging Black folks to ride bikes for its health benefits and for social interaction. I am the president and I help run the club along with my very capable board members. We lead rides, do a bike 101, and attempt to create a positive bike culture within and around Pittsburgh.

The Major Force Youth Cycling Program is a program that empowers youth through learning the skills of cycling safely on streets and bike trails, and benefits of a healthy lifestyle. The 10-week program ends with each participating youth receiving the bike that they have trained with as a reward. Our signature ride, the McDermott 3-State Tour (a longtime event generally held in July) is a fundraiser.

How can people get involved?

Folks can look us up at to join us on rides. You do not have to be a member to ride with us, but if you find you like riding with the club after several times, we strongly encourage folks to join to participate in the discounts, social activities and club insurance. Folks who just want to support can donate via our website as well.

The club’s been around for nearly 20 years. What do you attribute its success to?

My predecessor, Bruce Woods, definitely was instrumental in bringing a lot of folks in. Also, I would say consistency...having the amount of consistent rides that we do. During cycling season, there are at least two rides every week, which is pretty solid. Having ride leaders is hugely instrumental to our success. Nobody’s paid. Everyone donates their time. It’s a testament to the club and what we represent that we still exist even without having paid staff.

What motivates your involvement?

More Black folks finding joy. Folks that live and thrive, and not just survive.

Where do you like to ride around Pittsburgh?

Frick Park for mountain bikes. I like Roller Coaster Trail, Roller Coaster Extension and Dinky Bridge Trail and Iron Gate Trail. For road, through Larimer, Lincoln, Highland Park and to Riverview Park. The best rides are the ones that start from my house!

Pittsburgh is cold in the winter! Do you ride year-round?

I do, layering is key! Everyone thinks you’ve gotta buy a $300 kit just to ride outside. That’s not the case. Have the closest layer be dry-wicking and wool and then maybe have another [insulating] layer and have a shell to be the wind-blocking layer. Something to cover your face like a neck scarf or a balaclava—not to be confused with baklava! For gloves, I would say you could have a liner and one of those hand-warmer packs to put in and a thicker glove on the top like a mitten or a lobster claw so you can still maneuver your fingers and grab the brakes. Another bonus item are Bar Mitts—those are amazing.

What are The Black Foxes?

It’s a collective of Black individuals who aim to amplify our voices and activities positively in the outdoor space, however that looks. The main focus is cycling. Everyone’s doing things in their respective communities. I think my larger role with The Black Foxes is about broadening my impact within my community. I did the League of American Bicyclists LCI [League Cycling Instructor] course so I could be insured to lead classes on behalf of Major Taylor or any other endeavors we decide to do.

What’s your dream for how cycling could look in Pittsburgh?

To be more accessible in all areas; for the accessibility to reach not just the white neighborhoods, but the Black neighborhoods. The accessibility tends to start (in white neighborhoods) and doesn’t tend to reach the Black neighborhoods until gentrification starts. And then it’s tough because we’re a city of all these hills and it’s very, very tight with small streets, but [two keys are] having more accessible roadways and more traffic calming.

POGOH [Pittsburgh’s bikeshare system] is also here. [Including ebikes at the bikeshare stations] makes it so people who don’t ride hills as well get around. POGOH is doing an amazing job—and folks should and could support them by donating too! If we had POGOH in not just small parts of the city, to bring in that access everywhere: That would be amazing. 

All articles are for general informational purposes.  Each individual’s needs, preferences, goals and abilities may vary.  Be sure to obtain all appropriate training, expert supervision and/or medical advice before engaging in strenuous or potentially hazardous activity.