Test drive the all-new 2021 Harley-Davidson Sportster S motorcycle


Traveling as a digital nomad recently, I had the opportunity to test drive the all-new 2021 Harley Davidson Sportster S in Chicago. As a still honeymooning motorcycle entertainment reporter, I was thrilled to jump on a brand new Harley motorcycle. During the few weeks I rode it, the Sportster and I were the center of attention everywhere we went. The feel of riding this bike itself is unmatched, but what surprised me even more was the lifestyle and the community I was welcomed into.

To start
Since recent trips have been chaotic to say the least, I was fortunate to be an hour and a half by train from downtown Chicago to Harley-Davidson headquarters in Milwaukee to pick up the bike. I was greeted by Paul James, Public Relations Manager at Harley, for an introduction to the new 2021 Sportster S performance bike. To say I was impressed would have been an understatement – the Sportster embodied futuristic and conceptual design in a compact size, nodding to their iconic XR750 racing bike model. After a brief demonstration, Paul personally escorted me to the freeway where the Sportster S and I made our first drive on I-94, giving me the opportunity to admire the fields and landscapes of the Midwest. while I was browsing the fall to dusk thumbnails.

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 lineup,” said Jochen Zeitz, president, president and CEO of Harley-Davidson. “This is a next-generation Sportster defined by power, performance, technology and style. And that’s part of our commitment to introduce motorcycles that align with our strategy to increase attractiveness and carry on Harley-Davidson’s legacy. “

In the new age of travel and the lack of people-to-people interaction, I was delighted to have a companion as a digital nomad, and more so a bike that could easily fit into my lifestyle in a metropolitan city. Taking out the Sportster every day was an exciting way to break the boredom of working from home, and with a low seat height and super slim profile, the bike was a dream for maneuvering and cruising through Chicago. As a new morning routine, the novelty of admiring the bike never faded, namely the glittering Stone Washed White Pearl paintwork contrasting with the aggressive 16-inch tires and the exposed Revolution Max 1250T engine.

  • Parked in front of Philz Coffee while sipping my daily Americano, this bike clearly says, “Not your dad’s Harley.” The silhouette is unmistakably a redefined take on existing Harley Sportster models and a departure from traditional cruiser designs. Her style communicates not only power, but also confidence and thrill.

Sportster S 2021 – Photoshoot in Scotland

  • “Every visual design element of the Sportster S is an expression of the raw power of the bike,” said Brad Richards, Harley-Davidson vice president of style and design.


The 4.0-inch-diameter round TFT liquid crystal display was a key feature that made getting around Chicago smooth. The screen easily displays all of the information and entertainment options, including navigation, music and speedometer, all of which are associated with the Harley-Davidson® app. My favorite ride was down Chicago’s Lakeshore Drive, a freeway that runs along the shore of Lake Michigan through the city. The pockets at the bottom of Lakeshore were teeming with life and culture, but large enough where social distancing was hardly difficult. Speed ​​on Lakeshore is a reasonable 45 to 50 mph, bordered by over 15 miles of green trails, beaches, skyscrapers, and cultural attractions.

  • Blue skies along the Lakeshore

  • Fall foliage in Chicago’s Lincoln Park

  • One of the first trips I took was to watch the sunset over the horizon at Montrose Beach, Chicago’s largest man-made lakeside beach. Driving in gravel from the concrete road provided the perfect opportunity to use the interchangeable driving modes offered by the Sportster: road mode, speed mode, rain mode and custom mode. Pressing the Mode button on the grip instantly affects throttle, engine brake, traction control and ABS. I was able to immediately notice the difference between road mode and rain mode when the safety features kicked in. As a relatively new pilot, it was really reassuring to benefit from the additional safety improvements.

  • Sportster® S model infotainment: The Sportster® S model display supports infotainment via Bluetooth® with music, voice commands for making or receiving calls, turn-by-turn navigation and a speedometer.
  • Although the original model did not come with storage compartments, I was able to tuck into an AirTag in the bike. Since the steering is challenged, the built-in navigation and AirTag location made it easy to locate the bike wherever I went.

  • My go-to outfit was a structured yet lightweight lambskin All Saints motorcycle jacket paired with black jeans, Saint Laurent boots and a Louis Vuitton sling messenger that made it an easy and durable outfit for any occasion, Day and night.

  • Racing around town on the Sportster has always been an adventure. The convenience of parking is by far the biggest benefit of riding a motorcycle, especially in downtown Michigan Avenue, where I’ve always been able to find gaps on busy parked streets.

  • The Sportser S is nestled in the expansive downtown Chicago skyline.

New community

I’ve always been drawn to Motorcycle Culture and its Autonomous Community: a subculture of American rebels who don’t play by the rules. Despite being a somewhat experienced rider, I was skeptical of how the community would receive riders from different backgrounds like me. Granted, most of the bikers I saw in the media and in real life were stereotypically portrayed as tattooed and bearded, so I was naturally curious how I would fit in.

I was pleasantly surprised to be approached regularly by Chicagoans. Conversations and connections throughout my time with the Sportster were varied, ranging largely from curious to Harley enthusiasts. Plus, I was a millennial minority in the Midwest riding a Harley motorcycle, which I hope gives influence to prospective people looking to explore a new journey in this changing era of travel. Gradually, I started to feel included in a new community that I previously thought was inaccessible. The connection between the bikers was particularly remarkable, it was like entering a community with other men without stigma.

I believe the mere fact that I wasn’t a stereotypical beefy, bearded man on this bike was enough to grab attention, but the combination of what I stood for as a millennial living an alternate lifestyle made the even more interesting dynamic. The stark contrast between me and the regular Harley rider has taught me that there is not a single stereotypical Harley enthusiast.

Final thoughts

Traveling on the road presented a captivating and authentic image of the city of Chicago. Additionally, the idea of ​​being a motorcyclist transcended beyond a simple mode of transportation to become an extension of myself and how I influence and deconstruct the image of a previously thought-out exclusive community. Upgraded with technology and safety, the Sportster S is the perfect bike for a new generation of riders while connecting with its key customers, the power to perform and the ability to customize make it universally adaptable.

Personally, I am optimistic to see the future of riding as more inclusive, redefining motorcycle culture from traditionally male to all who are fearless, risk takers and adventurers. At the end of the trip, I’m surprised how a budding idea of ​​learning to ride a bike has affected such an integrated part of my travel identity. It was definitely a bittersweet farewell to complete the test lap.

About Harley-Davidson:
Harley-Davidson, Inc. is the parent company of Harley-Davidson Motor Company and Harley-Davidson Financial Services. Our vision: Build our legend and lead our industry through innovation, evolution and emotion. Our mission: More than building machines, we are 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, rider gear and apparel. Harley-Davidson Financial Services offers financing, insurance and other programs to help drivers get on the road.

The 2021 Harley-Davidson line of motorcycles, the Sportster S, is now marketed through Harley-Davidson dealers starting with a starting MSRP of $ 14,999.


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