Motorcycles are a huge part of my life, and over the years I’ve owned six different Harley-Davidsons models. My rolling resume includes a 1997 Sportster, 2001 Super Glide, 2010 Wide Glide, 2012 Road King and my current ride, a 2017 Street Glide Special.
All my Harleys were purchased at Harley-Davidson Winnipeg. David and Sheryl Gray, the dealership owners, and their capable crew of enthusiastic staff, always treat me like family. I’m never in a hurry at the shop, there’s so many cool bikes in the showroom and the majority of my wardrobe was also bought there. All my Harleys have been reliable and also held their value much better than the many cars and trucks I’ve owned.
If you’ve been dreaming about owning a Harley-Davidson, but have no idea where to start, here’s a quick lowdown on all the Harley models. If you want to see these beautiful bikes in person stop by Harley-Davidson Winnipeg for a visit, but take my word for it, you’re gonna want to set aside a couple of hours to see it all.
For most of Harley’s history the Sportster has been the smallest motorcycle in its lineup, but back in 2014 the all-new Street was introduced, and has since become a popular entry-level model.
Three Street models are available for 2020: Street 500, Street 750 and Street Rod (750). The most affordable bikes in the lineup, Street models start at $6,999.
The legendary Sportster has been in the Harley lineup since 1957.
Many longtime Harley owners got their start on a Sportster. Thanks to nimble handling and a seemingly endless supply of parts and accessories, Sportsters are also popular in the custom world and have had a resurgence of popularity among younger riders.
Sportster models available for 2020: Iron 883, Iron 1200, Forty Eight (1200) and Roadster (1200). Sportster models start at $11,499.
In 2018 Harley-Davidson discontinued its Dyna model and subsequently expanded the Softail lineup.
As a result there are now 11 Softail models to choose from, ranging from the popular and affordable Street Bob all the way up to the iconic and powerful Fat Boy 114. Engine choices in the Softail lineup include either the Milwaukee-Eight 107 or the Milwaukee-Eight 114.
Softail models for 2020: Street Bob, Low Rider, Softail Slim, Sport Glide, Deluxe, Heritage Classic, Lowrider S, Fat Bob 114, FXDR 114, Fat Boy 114 and Breakout 114. Softail models start at $16,999.
If you plan to do some cross-country riding, or enjoy listening to tunes while rolling down the highway, the Harley-Davidson Touring models, or Baggers as they are often referred to, have become extremely popular in recent years.
Engine choices in the Touring lineup include either the Milwaukee-Eight 107 or Milwaukee-Eight 114, and the Twin-Cooled Milwaukee-Eight 114, which has liquid-cooled cylinder heads.
The Road Glide models, nicknamed a Sharknose, are unique in that the front fairing is attached to the frame and does not move when the handlebars turn. The BOOM! Box GTS infotainment system provides exceptional sound and car-like features such as navigation and Apple Carplay. Touring models for 2020: Road King, Road King Special, Street Glide, Street Glide Special, Road Glide, Road Glide Special, Road Glide Limited, Electra Glide Standard and Ultra Limited. Touring models start at $23,699.
If two wheels aren’t enough and four are too many, a Harley-Davidson Trike may be just right for you.
The Freewheeler is a stripped down three-wheeler with a Milwaukee-Eight 114 and the attitude of a Road King, while the Tri Glide Ultra is a fully loaded touring machine powered by the Twin-Cooled Milwaukee-Eight 114.
Trike models start at $33,999.
The CVO or Custom Vehicle Operations models are the top-dogs in the extensive Harley-Davidson lineup.
Built in limited numbers and featuring a powerful Milwaukee-Eight 117 engine, CVO models offer show-stopping finishes, advanced technology, exclusive components, and attention to detail that borders on obsessive.
CVO models for 2020: CVO Street Glide, CVO Limited and CVO Tri Glide. CVO models start at $49,799.
In addition to the traditional motorcycles Harley-Davidson has been building since 1903 — 2020 and beyond promises some exciting and interesting bikes including the Live Wire electric motorcycle, the Bronx sport bike, the Panamerica, an adventure touring bike, and even a lineup of electric bicycles.
Paul “Willy” Williamson joined the Free Press editorial team in 2007, turning his back on a career as a corrections officer. His motor has been running non-stop ever since.