Recently traveling as a digital nomad, I had the opportunity to test ride the all-new 2021 Harley Davidson Sportster S in Chicago. As primarily an entertainment journalist still in the honeymoon phase of motorcycling, I was ecstatic to jump on a brand new Harley bike. During the few weeks I rode it, the Sportster and I were the center of attention everywhere we went. The feeling of riding on this bike itself is unrivaled, but what surprised me even more was the lifestyle and community I was welcomed to.
As recent travel has been chaotic to say the least, I was lucky enough to be a short hour and a half train ride from downtown Chicago to the Harley-Davidson Headquarters in Milwaukee to collect the bike. I was welcomed by Paul James, PR Manager at Harley, for an introduction to the new 2021 Sportster S performance motorcycle. To say that I was in awe would have been an understatement – the Sportster embodied a futuristic, conceptual design in a compact size, taking a nod from their iconic XR750 model racing bike. After a brief demo, Paul personally escorted me to the freeway where the Sportster S and I had our initial ride down the I-94, giving me an opportunity to take in belts of the Midwestern fields and scenery as I cruised into the vignettes of the fall dusk.
A New Companion
“The Sportster S is the next all-new motorcycle built on the Revolution Max platform and sets a new performance standard for the Sportster line,” said Jochen Zeitz, Chairman, President and CEO, Harley-Davidson. “This is a next generation Sportster defined by power, performance, technology and style. And it’s part of our commitment to introduce motorcycles that align with our strategy to increase desirability and to drive the legacy of Harley-Davidson.”
In the new age of travel and lack of interpersonal interaction, I was overjoyed to have a companion as a digital nomad, and even more so a bike that could transition easily into my lifestyle in a metropolitan city. Taking the Sportster out every day was an exciting way to break up the tedium of working from home, and with a low seat height and ultra slim profile, the bike was a dream to maneuver and cruise through Chicago. As a new morning routine, the novelty of admiring the bike never wore off, namely the glistening Stone Washed White Pearl paint contrasted against the aggressive 16 inch tires and exposed Revolution Max 1250T engine.
- Parked outside Philz Coffee while sipping my daily Americano, this bike definitely says, “Not your dad’s Harley”. The silhouette is unquestionably a redefined vision of the existing Harley Sportster models and departure from the traditional cruiser designs. Its styling communicates not only power, but confidence and thrill.
- “Every visual design element of the Sportster S model is an expression of the motorcycle’s raw power,” said Brad Richards, Harley-Davidson Vice President of Styling and Design.
The round 4.0-inch-diameter TFT liquid-crystal screen was an essential feature that made traveling around Chicago seamless. The screen displays all of the information and entertainment options easily, including navigation, music, and speedometer, which all pair to the Harley-Davidson® App. My favorite ride was cruising down Chicago’s Lakeshore Drive, an expressway running alongside the shoreline of Lake Michigan through the city. Pockets down Lakeshore were abuzz with life and culture, but vast enough where social distancing was hardly difficult. The speed down Lakeshore is a sensible 45-50mph, bordered by over 15 miles of green trail, beaches, skyscrapers and cultural attractions.
- Bright blue skies along Lakeshore
- Fall foliage in Chicago’s Lincoln Park
- One of the first trips I set out on was to catch the sweeping sunset views of the horizon at Montrose beach, Chicago’s largest man-made beach on the lakefront. Driving into gravel from the concrete road allowed for the perfect opportunity to utilize the interchangeable ride modes that the Sportster features: Road Mode, Speed Mode, Rain Mode, and Custom Mode. Pressing the Mode button on the handle instantly affects throttle, engine braking, traction control, and ABS. I could notice immediately the difference from Road Mode to Rain Mode as the safety features kicked in. As a relatively new rider, it was definitely reassuring to have the additional safety enhancements.
- Sportster® S Model Infotainment: The Sportster® S model display supports infotainment via Bluetooth® with music, voice commands to place or receive calls, turn by turn navigation, and a speedometer.
- Although the stock model doesn’t come with any storage compartments, I was able to nestle in an AirTag in the bike. Being directionally challenged, the integrated Navigation and AirTag location made it seamless to locate the bike wherever I went.
- My go-to attire was a structured but lightweight lambskin All Saints Motorcycle jacket paired with black jeans, Saint Laurent boots, and a Louis Vuitton crossbody messenger that made for an easy and durable outfit for any occasion day or night.
- Running errands in the city on the Sportster was always an adventure. The convenience of parking is easily the biggest benefit of riding a motorcycle, especially in downtown Michigan Avenue where I was always able to find gaps on the busy parked streets.
- The Sportser S nestled in downtown Chicago’s expansive skyline.
I was always enticed by the Motorcycle Culture and its self-contained community: a subculture of American rebels who don’t live by the rules. Despite being a somewhat experienced rider, I was skeptical of how the community would receive riders from different backgrounds like me. Admittedly, most bikers I’ve seen in media and in real life were pictured stereotypically as tattooed and bearded, so I was naturally curious to know how I would fit in.
I was pleasantly surprised by being approached regularly by Chicagoans. The conversations and connections throughout my time with the Sportster were varied, largely ranging curious bystanders to Harley enthusiasts. In addition, I was a millennial minority in the Midwest sporting a Harley bike, which I hope gives influence to perspective individuals looking to explore a new journey in this changing age of travel. Progressively, I began to feel included in a newfound community that I previously thought was unavailable to me. The connection between bikers was particularly noteworthy, it felt like gaining access to a community with other men without a stigma.
I believe the fact alone that I wasn’t a stereotypical burly and bearded man on this bike was enough to capture attention, but the combination of what I represented as a millennial living an alternative lifestyle made the dynamic even more interesting. The stark contrast between myself and the regular Harley rider taught me that there is not one stereotypical Harley enthusiast.
Traveling on the road presented a captivating and genuine picture of the city of Chicago. Additionally, the idea of being a motorcyclist transcended beyond solely a mode of transportation to an extension of myself and how I influence and deconstruct the image of a previously thought exclusive community. Enhanced with technology and safety, the Sportster S is the perfect bike for a new generation of riders while also connecting with its core customers, the performance power and ability to customize makes it adaptable universally.
Personally, I’m optimistic to see the future of riding as more inclusive, redefining the motorcycle culture from traditionally masculine to all people who are fearless, risk takers, and adventurers. At the end of the journey, I am surprised how a nascent idea to learn to bike affected such an integrated piece of my journeyed identity. It was definitely a bittersweet farewell to end the test ride.
Harley-Davidson, Inc. is the parent company of Harley-Davidson Motor Company and Harley-Davidson Financial Services. Our vision: Building our legend and leading our industry through innovation, evolution and emotion. Our mission: More than building machines, we stand for the timeless pursuit of adventure. Freedom for the soul. Our ambition is to maintain our place as the most desirable motorcycle brand in the world. Since 1903, Harley-Davidson has defined motorcycle culture by delivering a motorcycle lifestyle with distinctive and customizable motorcycles, experiences, motorcycle accessories, riding gear and apparel. Harley-Davidson Financial Services provides financing, insurance and other programs to help get riders on the road.
The 2021 Harley-Davidson motorcycle line, the Sportster S is now Harley-Davidson dealers starting at a base MSRP of $14,999.