Harley-Davidson and "beginner-friendly" are not phrased typically spoken in the same breath, but that is changing. For decades, the history of Harley-Davidson was one of expensive, ostentatious, and hard to handle bikes, which only skilled riders would even dare to entertain. These were 700-pound behemoths with chrome everything and massive, rumbling V-twin engines. They had torque curves that looked more like cliff faces than a gentle hills. But the Milwaukee company has realized, presumably, in the past
two decades that not every rider wants to spend years on other bikes before getting their Harley wings.
To that end, Harley has been making (some) machines that actually have reasonable weight, a predictable power delivery, and modern safety features — things new riders need to survive their first few thousand miles. What's more, the brand has done this while maintaining that classic Harley-Davidson experience. After all, beginner-friendly doesn't mean watered-down, boring or compromised.
These bikes still sound like proper Harleys, still turn heads at traffic lights, and still perform. They're just engineered to be less likely to kill you while you're learning the ropes. The best part? You won't outgrow them quickly. These Harley motorcycles can remain your go-to bike for years of riding adventures.
Read more: 6 Of The Fastest Cruiser Motorcycles, Ranked By Top Speed
2014+ Street 500
The Street 500 is one of those Harley-Davidson models that we all love hating on. However, it is a brilliant entry-point to the Harley universe, offering manageable weight and power. Coming in at 514 pounds wet, it's one of the lightest Harley bikes that you could get. What makes the Street 500 a great bike for beginners is the low seat placement (28 inches), manageable weight, and linear torque delivery; meaning it's one of the few Harley's that won't jump or lurch at high accelerations that novice riders tend to do. You can pretty much ignore the RPM meter and the bike won't punish you for it. Ignore the perfect RPM on a CVO Road Glide, for example, and you'll end up in a ditch with a 900 pound bike on top of you.
Another aspect of the Street 500 is the price, as decent examples can be had on the used market in the range of $4,000 to $6,000, meaning that it won't break the bank to obtain one. However, do note that since the Street 500 is no longer in production, having been introduced in 2013 as a 2014 model, and discontinued in 2020, it will only get harder to find OEM parts for the bike. If that is something that you're okay with, and don't particularly want to drop more cash for a more expensive model; then the Street 500 is the perfect entry point into the Harley universe.
2014+ Street 750
The Harley-Davidson Street 750 has more power, more weight, more features, and more comfort, but it does take a bit more skill to ride. In essence, it is the bigger brother to the Street 500, for beginner riders who aren't completely wet behind the years. Though pricier, the 750 is a much better investment long-term, kind of like buying a better camera as an amateur knowing you'll get better with time and be able to get more out of your purchase down the line.
Where the S500 came with a 30 cubic inch Revolution X engine, the 750 comes with a larger 45.7 cubic inch unit. This bigger, more rumbly V-twin makes 58 hp versus the 500's 36.2, and 43.5 lb-ft of torque versus the 29.5 on the Street 500. What's more, on the 750, this torque is available from just 4,000 RPM, meaning that it has plenty of oomph from basically the get go; so not having to redline the tachometer when overtaking. It's a subtle difference that has a huge real world impact.
Other notable features on the 750 include its cast aluminum wheels, electronic speedometer, 55 mpg economy, and optional ABS. However, the Street 750 is a discontinued model, with production ending in 2020, which means the only way to snag one is to look at the aftermarket, where prices hover around the $4,000 mark.
2025 Trike Freewheeler
The Harley-Davidson Trike is arguably the most beginner-friendly bike on this list, because it is, by default, much more stable than a regular motorcycle. As the name suggests, the Trike has three wheels, meaning it balances itself without input from the rider. What's more is that it comfortably seats a second passenger, making it one of the best Harley-Davidson models for two people currently on the market. Production for the Trike began in 2009, and is still going strong today, with two main versions being offered. The first is the Trike Freewheel, which is the standard version, coming in with a base MSRP of $32,599. The second one is the significantly upgraded Tri-Glide Ultra that adds a lot more storage, special paint schemes, back and arm support for the pillion rider, and other quality-of-life upgrades for the open road.
Of course, the Tri-Glide Ultra does command a premium over the regular Trike Freewheel, coming in at $38,849 before options — but for those willing to make a long term investment, it's fantastic. Both Trike models share the same powerplant, which is the Milwaukee-eight 114 displacing 114 cubic inches — hence the name — making 83 hp and 116 lb-ft of torque. Key talking points for the Trike Freewheeler are its seven-system rider aid suite, 36 mpg economy, trip computer, and the inclusion of a reverse gear. If you plan on making several long-distance trips, then consider upgrading to the Ultra, or investing in additional storage on the Freewheeler through aftermarket upgrades.
2025 Sportster S
The Harley-Davidson Sportster S is a little on the smaller side compared to the other bikes on this list. It's been available since 2021, and current generations come with the Revolution Max 1250T engine that churns out a respectable 121 hp and 92 lb-ft of torque, with peak hp available at 7,500 RPM. Furthermore, the Sportster S comes in with a weight of just 503 pounds — which is about as light as a modern Harley is going to get — meaning that it is very maneuverable. The seating position being 30 inches above the ground is also a plus point for new riders, because it means that the center of gravity is lower, and it's easier for riders' feet to reach the ground to re-balance.
Turning, which is a pain point for new riders will also be easier, as riders can use their feet to help "pivot" the bike if unbalanced. The base MSRP for a 2025 Sportster S is $16,499 — and that's before customization. If that base MSRP looks ridiculous, it is. That's why buyers could — and should — also look to save a lot of money by checking out used Sportster S models on the used market, where prices for 2021 models begin at $8,000 — comparatively a bargain. However, with the many variations that are available, make sure you select a Harley that is the right size. No matter whether buyers opt for a used or brand-new Sportster S, one thing's for certain: they won't be disappointed.
2025 Street Bob
The last affordable, beginner-friendly Harley-Davidson on our list is the Street Bob. Technically, this is part of the Harley Softail family, and comes with a body style that is known as a "bobber" in enthusiast circles. It has the 117 Milwaukee-Eight engine making 91 hp and 115 lb-ft of torque, and can seat two passengers. Points worth talking about on the 2025 Street Bob include the dual-bending suspension, seven different driver aids, selectable riding modes, and USB-C charging. It is one of the more comfortable Harleys to ride, and is also fairly maneuverable, at 91 inches long. The fuel tank holds 3.5 gallons, and with an EPA estimated fuel economy of 42.7 mpg, riders can expect to get around 150 miles between fill-ups.
A new 2025 Street Bob would run buyers $15,999, and that's if the special paint schemes are not opted for. That said, a lot of great deals can be had by buying used Harley-Davidsons these days, so that's also an option worth looking into. For instance, where a 2025 Street Bob costs around $15,999, a used model from 2015 can be had for around $8,000 — which is an instant savings of $8,000. Beginner riders can, and should put this money towards upgraded safety gear and maybe even a couple biker tours and trips, as these are experiences worth investing in.
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