The Quintessential American Motorcycle

Some 20 years ago a riding buddy asked me, “If you could own any one road bike for trips, around town, day riding, whatever, what would it be?” I gave that some thought, then replied, “I think I’d choose the Harley-Davidson Heritage Softail Classic. I just love the American tradition meets modern in that bike.” I found myself on a 1998 Yamaha Royal Star Tour Classic for many years, that brand’s answer to the Heritage, and loved it, but the H-D Heritage was always the original to me. My father later bought one, a 2003 100-Year Anniversary edition in silver/black, and he rode it with my mom all over the Southeast USA until his age and health forced the sale of the bike. I had a garage full at the time, but regretted not buying it from him. Such a beautiful, smooth, cool machine. Motorcycle Americana at its best.

The first time I rode one of the newer iterations of the classic model in the Harley universe was at a press launch in Oxford, Alabama in September of 2018. I took a 107 ci Road King out for a couple of hours, and found it to be a real hooligan bagger. Had a great time blasting through the hill country of northeast Alabama on it. When I returned to throw a leg over the 114 ci Heritage and lit out down the same roads, the bike practically spoke to me, “Whoa cowboy, take it easy. Let’s enjoy the ride and the countryside this time.” I obeyed, and came to love the relaxed lope and feel of the classic yet modern vibe of the Heritage.

Pop’s 2003 Heritage, and out with Mom on a ride astride it.

Fast forward to June 2021, and I was headed up for the MotoAmerica races at the famed Road America track in Elkhart Lake, Wisconsin. I reached out to our friends at Harley-Davidson, and they offered me the chance to ride a brand new 2021 Heritage for the long weekend. I could not have been more thrilled. Nathan “GenZ Biker” Baron picked me up at the airport and transported me to Harley HQ, where they had this beautiful, brand new (barely 57 miles on it) crimson and pearl Heritage under a shade tree, awaiting my acquaintance. I would be living off the bike for the next three days, so I transferred my gear to the mounted leather-wrapped hard bags of the bike, each of which have nice capacity. Harley PR boss Paul James gave me the 411 on the bike, after which I followed Nathan through the city streets to the Fuel Cafe’ for lunch, then hopped on the highway to roll north toward Elkhart Lake.

For my first ride on the new Heritage, negotiating the streets of Milwaukee was effortless, as the bike felt light and nimble. For 2021, the Heritage is of course sporting the Milwaukee Eight powerplant with a 6-cog gearbox, and has both lost and gained- This Heritage is 41 lbs lighter than the previous version, and has gained an inch or so of ground clearance, making it surprisingly flickable for a large cruiser/tourer. Motoring north on I-43 out of the city, The throttle roll-on was smooth yet powerful in each gear, merging and rolling with the city’s Friday interstate traffic. Given the newness of this particular bike I was straddling, I found the shifting to be a bit clunky and had trouble finding neutral several times that day, which is not uncommon until these bikes get about 500 miles on the ODO, when everything has begun to settle and seat. Once they do, Harleys are well-respected for their solid yet butter smooth clutch and shifting.

Random snaps from Milwaukee to Road America.

The 2021 Harley-Davidson Heritage Classic comes in two variations- the 107 ci (which I had) slathered in chrome from stem to stern with a chrome round air cleaner cover, just like its chromed-to-the-hilt ancestors. The 114 ci is blacked-out front to back, except the pipes and a blacked oval air cleaner. With eight distinct color schemes between them, both versions are definite H-D eye candy, in my opinion. Both Ryan and Gerard, our photographers, couldn’t help but shoot a ton of photos, both quipping, “It’s such a beautiful bike.” High praise from a pair of sportbike and ADV riders, respectively. Did I mention this color scheme? They call it “Midnight Crimson/Stone Washed White Pearl.” I call it gorgeous.

I pounded pavement north on I-43 until it split east, then continued on WIS-57 North toward the little hamlet of Plymouth. Traffic all but disappeared as I found myself riding through Wisconsin farm and dairy country, with gently rolling hills, miles of crop and pastureland, and little population. Turning into a roadside convenience store, A local dairy delivery guy pulled alongside in his company truck and chatted me up about the Heritage, and his own love of motorcycling. Like everyone I met, he had this unique Great Lakes accent coupled with a down-home country friendliness.

I decided to take the long way to my AirBnB in Plymouth, a couple of miles from the track. Since the racing was officially kicking off the next morning, I thought I might enjoy meandering through the back farm roads, many with only letters as designation- County J, County E, and so on. The Heritage was the perfect companion for the pace of life out there, loping along, drinking in the beautiful views and enjoying the ride. Motorcycling is both relaxing and invigorating for me, as I am focused and peaceful at the same time. The Heritage encourages that synergy, with its comfortable, neutral riding position, relaxed reach to the bars and perfect floorboard position, as well as its broad power spread and tune. My blood pressure mellowed and my heart rate relaxed every time I threw a leg over this Heritage.

One sexy Harley. Photos by Gerard Saraber

Arriving at Road America, I once again met up with Paul from Harley, and Joe Gustafson who works with him, to discuss the Motor Company’s partnership this year with the MotoAmerica road racing series, and specifically their factory support of brothers Kyle and Travis Wyman, racing Harleys in the King of the Baggers competition. Good to see Harley-Davidson officially back in racing, both in MotoAmerica and in American Flat Track. The Motor Company cut its teeth in its early years on racing, and is still very much in their DNA. Around the track all weekend, the Heritage I rode garnered much attention, questions and comments, due to its abundant chrome and killer paint scheme.

Saturday was a simply perfect day for riding, so I left the track mid-morning to early afternoon for some seat time through the countryside. Elkhart Lake is just up the street from the track, with a resident population of barely 1000, but rich in racing history. In the 1950s, the little hamlet played host to numerous road races on public county roads, both automobile and motorcycle, and placards around town attest to the racing that roared out into the countryside from the otherwise quiet little community. Elkhart Lake is also home to the exceptional Throttlestop Motorcycle and Classic Car Museum, with whom we’ve collaborated numerous times for our “Legendary Bikes” stories.

Ryan and Gerard helped me shoot some great photos and footage in and around the historic town, and as they returned to the track to continue covering the MotoAmerica race action, I couldn’t help but wander off with the Heritage to explore some more, for the enchanting Wisconsin vistas and the pure pleasure of riding this bike. So easy to maneuver around in the small towns I rode through, as well as around the small roads circumnavigating the 4 mile, 640 acre complex that is Road America, yet so smooth and comfortable out on the roads in wide open Wisconsin, the Heritage is everything one would need to road trip with, and nothing unnecessary. With all the on-board, dash-mounted electronics found in nearly every brand’s touring bikes today, It’s refreshing to just have a windshield in front and nothing else to distract from focus, and detract from the experience of bike and rider.

In and around Elkhart Lake, Wisconsin. Photos by Ryan Nolan & Gerard Saraber.

I was granted the unique and fun opportunity to race announce for the MotoAmerica Motul Mini Cup races over on the complex’s technical Kart track, and enjoyed employing my old radio pipes for calling the six races in this AMA and FIM sanctioned competition for young racers 8-14 years old. Upon departure I rolled east to Sheboygan, on the coast of Lake Michigan, for a late dinner and beverages at the popular Prohibition Bistro with Road Dirt guys Ryan and Gerard. Riding back to my weekend domicile in the gathering dark, I reveled in the relaxing cadence of the 107 ci V-Twin, eating the highway miles as I rolled west on WIS-23. The main headlight and two highway lights illuminate the road well ahead, while lighting up left and right enough to be well aware of movement coming from either side. Pulling back in after dark, I felt that distinct fatigue yet deep satisfaction one experiences after a very good day of motorcycling. I sat on the side of the bike for a few minutes before gathering my gear to go inside, listening to the ticking of the hot engine now silenced, and observing the fields and trees surrounding the farm house twinkling with fireflies, as if in silent celebration of my day astride the Heritage. My watch indicated 10pm local time, and yet it seemed like the day had flown by too fast.

Sunday came and with it, my departure back for Milwaukee. I should have booked an extra day, for the last of the races and the regional riding- duly noted for next time. After spending the morning trackside, I gathered my gear, bid adieu to the beautiful AirBnB farmhouse I’d called home for 3 days, and made my way back south toward Milwaukee. I enjoyed the ride and the bike until I-43 brought me close to the city. The interstate tarmac was terrible. Potholes, open cracks and crevices, and what I’m assuming was frost heave damage from the harsh Great Lakes winters. The road was absolutely jarring to ride over in many places. I got turned around a bit on the surface streets in downtown, but never felt overwhelmed with switching street to street on the Heritage- I found it easy to maneuver at slow speeds, doubling back on myself if I missed a side street, or negotiating construction zones and canal bridges. It certainly doesn’t feel its claimed curb weight of 728 lbs. I was about an hour early to drop the bike off at Harley HQ, so I rode over to the Harley-Davidson Museum for a drink and snack at their Motor Bar & Restaurant. When in or near Milwaukee, you really should make time for a tour of the Museum. We’ve been through it a couple of times, and whether or not you ride a Harley, the Museum is an extraordinary stroll back through American motorcycling history, from the standpoint of the Motor Company’s many contributions to our beloved pastime. And the fixin’s at the Motor are quite delish.

Beautiful sunset at my AirBnB, and a shot in front of Harley HQ

I returned the bike to Harley-Davidson’s headquarters on Juneau Ave, after shooting a short conclusion clip for our video review (below). Nathan picked me up to ferry me to the airport, and we discussed on the way the Harleys we’ve both had the pleasure to ride over the years. You’ll have to check out his review last year of the Sport Glide– lots of great onboard ride footage. I confided to him that I’d recently sold my old Yamaha Royal Star Tour Classic, and written off big heavy cruisers and tourers. “I’m getting older, and they’re getting heavier,” I quipped. Yet after a long weekend with the Harley Heritage, I was reconsidering my position. I felt so comfortable on the bike, found it so easy to maneuver around at any speed and in any setting, and so loved the smooth power delivery and ride of the bike, I’ve come back around to the original answer to my old friend’s question some 20+ years ago- I think I’d choose the Heritage Classic. Again.

For more on the Harley-Davidson Heritage Classic, click here:

Heritage Classic

For more on the MotoAmerica racing series, click here:


If you’re looking for a wonderful place to stay around the Road America track, check out my friends Jack and Elise:

Plymouth Farmhouse


*Be sure to check out our ride/review below, without ever leaving this page-


  1. Clifton Ray Gregg

    I love the Harley Heritage Classic. I started riding Harleys in 1978 on a new Super Glide and fell in love with the Harley brand. My next bike was 82 Wide Glide and I rode it for 22 yrs. From there I progressed to a Fat Boy my first softail. Since that bike I have owned and rode with much comfort and pride three Heritage Softail Classics, a 2005, a 2012, and a 2017. For a short legged person this bike is awesome. The maneuverability, the comfort and just the feel of the bike should win anyone over. Between my 3 Heritages I accumulated 180,000 miles look forward to the next 180,000 good Lord willing and the creek don’t rise. Live to ride.

    • Rob Brooks

      You’re a true Harley “Motor Head”, in brand and miles! Thanks for sharing a bit of your story, sir. Ride on.

      • Ralph Webb

        Lots of back ground noise. Hard to hear at times.

        • Rob Brooks

          My apologies, we discovered just how muffled one section of audio was once we returned to Georgia. Cleaned it up as best we could, but we’ll have that issue fixed by the next bike eval.
          Thanks for reading the article!

  2. Robert Smith

    Very informative, entertaining and well written article! As noted above, video was almost too difficult to follow due to wind noise. Quick fix to that and you’re back in business! Looking forward to reading and watching more!

    • Rob Brooks

      Yeah, discovered the wind nose problem, esp on one particular clip, after I returned home with the footage.
      Rectified for future reviews. Thanks Robert!


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