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I'm trying to figure out whether to go with a Chieftain or the Challenger. I'm going to trade in my 60 and need something bigger. So I'm asking for some detailed opinions from people who have experience with one or both of these models.
Planned typical riding is around 250 miles in a run with a lot of highways and intercoastal waterway bridges. I'm looking for comfort, reliability and obviously safety.
Any input would be great.
 

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Either are great machines, it's all in your riding preference and style. I had an 18 Roadmaster that I rode 90% of the time with no trunk so basically a Chieftain. I now have a Challenger, even my wife after riding on the back said " I see why you wanted this bike its way more fun". I don't feel like the Challenger sacrifices in comfort in the slightest. Really the best thing you can do is go ride them back to back.
 

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Both excellent bikes. Some pros and cons with either. Ride them yourself, get as much seat time as you can. I'd be happy with either bike. Better yet it'd be awesome to have both.
 
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I have a Chieftain and love it, the heated seat is so nice. all depends on you, get what you want, you are the one that will live with the decision - I know, no help...
 

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Like @n.idahorm said, I have a Roadmaster that is ridden without the trunk, aka Chieftain configuration. If I were riding 2-up, I think the trunk is a better configuration. Riding solo, I like using a sissybar/luggage rack. However, I still like the hard lowers.

My wife rides a Chieftain. She is quick to tell you how comfortable it rides -- compared to her Fatboy. A 250 mile trip on either of our 111 bikes, is just an afternoon hop. Just a little more than a tank of gas.
One item she reported that I don't seem to have was some buffeting. After installing a LRS flip windshield it continued. We were stumped until we figured out the wind was coming up under the fairing. A pair of deflectors fixed that.

While I have yet had an opportunity to ride a Challenger, I would like to try one. I think you will be happy with either.
 
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If you riding mostly on highway, then I would recommend Challenger because this is what they design to, lots of power when overtaking vehicles during highway speed.
 

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I'm trying to figure out whether to go with a Chieftain or the Challenger. I'm going to trade in my 60 and need something bigger. So I'm asking for some detailed opinions from people who have experience with one or both of these models.
Planned typical riding is around 250 miles in a run with a lot of highways and intercoastal waterway bridges. I'm looking for comfort, reliability and obviously safety.
Any input would be great.
Chieftain 'all day every day' it's just MHO cannot get past that fairing.
 

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The Chieftain fairing has changed along with the saddlebags. Some like the newer style better and some like the original or Classic as it's called now better. I had a 2015 with the original fairing and had no buffeting issues at all. I don't have any experience with the new style one nor have I ridden a Challenger yet. I'm hoping there will be a demo event this year.
 

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What is your riding style? If all else is equal, a challenger will suit you if you are use it for spirited and floorboard dragging runs. If it's more of a relaxed, not in a hurry and taking in the scenery, then maybe the chieftain is a good fit. Both will do well at either task, but they will excel at their purpose.
 

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My vote goes for Chieftain, and if classic better, is not that i dont like the Challenger, is that i got the Sixty the first year and had to deal with lots of bugs and warranty claims, so i would wait a bit for all that stuff to get sorted out.
 

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A bike is like a woman . if it's all you think about and you no matter how much you ride it you still want to climb on also when you walk away you can't help but turn around and smile that's the one
 

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My vote goes for Chieftain, and if classic better, is not that i dont like the Challenger, is that i got the Sixty the first year and had to deal with lots of bugs and warranty claims, so i would wait a bit for all that stuff to get sorted out.
I got to agree. I would wait for a few years to work the bugs out of the Challenger. The Chieftain is tried and true. Got to admit, I don't care for the newer fairing on the new Chieftains. Makes me want to call them a Chiefglide. Dean
 

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A bike is like a woman . if it's all you think about and you no matter how much you ride it you still want to climb on also when you walk away you can't help but turn around and smile that's the one
If only it was easier to go out and do a test ride before deciding! LOL D
 

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I got to agree. I would wait for a few years to work the bugs out of the Challenger. The Chieftain is tried and true. Got to admit, I don't care for the newer fairing on the new Chieftains. Makes me want to call them a Chiefglide. Dean
Thats the reason i got the classic, i prefer the round look and the blinkers on the fairing over the new chiefglide style, its just not my cup of tea
 

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I chose the 2019 Chieftain Limited over the 2020 Challenger for a couple of reasons:
1. The 19 Limited was 23k out the door which was about 5k cheaper than a similar loaded Challenger.
2. The 20 Challenger was a little better in every area except it had too many bugs reported on the forums which I could not get past. Maybe in a few years I will look at the Challenger again.

Tim
 

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Challenger is a bit better performance but equal in comfort. A tad more lively handling and a bit more acceleration. The Chieftain a bit more of the classic V-twin sound. The 116 kit on mine negates the acceleration advantage of the Challenger. Lighter steering with the fixed fairing and at least for me not as attractive as the Chieftain from the walk around standpoint. But then again I think the Challenger looks great. I would be happy with either. It is great that Indian is making multiple options available.
 

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Personally, I think you made the right decision. If only because the same decision I would've made ! ! !





BD
 

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If you can swing it.......like I did......go with BOTH......then you get the best of BOTH bikes! In full disclosure, since I bought my Challenger, my Chieftain has seen ZERO miles. For me, it's all about performance, handling and ride quality. Don't get me wrong, Chieftain was/is a nice riding bike with a decent ride....but when compared with the Challenger (at least for me!) it's a NO brainer. Challenger is clearly a better riding and handling bike.....by far.
 
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