Just got back from a week of riding colorado. Mile high Harley is probably the closest dealer to the airport. Mt Evans is a fantastic ride and is close to Denver. After that you could take 40 east over Berthoud pass and at Granby choose Steamboat or Rocky mtn national park to Estes. That could all be done in a day. I did pikes peak $24.00 and mt Evans $10.00 and for less than half the cost we thought mt Evans was better.

Plan on riding early because the afternoon has more thunderstorms.

 

You know other than to say you did it, Pikes Peak really isn't all that pretty of a ride. There is much better stuff on into Colorado, you know Ouray, Silverton, Durango. The Rocky Mountain National Park and Estes Park are worth the time but it will be damn near impossible to work all that in in the time you have, getting to the southwest corner of Colorado, ie. Durango will take a solid day in itself. I don't know if Durango Harley rents bike any longer but it may be worth a check and try to fly into Durango.

 

What time do you arrive in Denver? Try to be there earlier rather than later. Day 1: Pick up your bike and ride to Estes Park for the night (you'll never experience anything like the elk rut and their bugling in town). Day 2: Drive over Trail Ridge Road, south over Berthoud Pass, west over Loveland Pass, south over Hoosier Pass, through South Park and spend the night in Salida. Day 3: Drive west over Monarch Pass, go through Gunnison, turn south at Montrose and head down to Ouray and over Red Mountain, Molas and Coal Bank Passes to Durango. Day 4: Drive east over Wolf Creek Pass, turn north at South Fork, drive over Slumgullion Pass to Lake City and back to Gunnison - if you arrive in Gunnison early enough you can drive north to Crested Butte for dinner. Day 5: Gunnison over Monarch (again) to Salida...drive down the Arkansas River Canyon to Penrose, turn north on Hwy 115 to Colorado Springs...continue north on I-25 to I-225 in Denver...return to Mile High HD. There are a couple other places to visit depending on time, etc. but this list hits some pretty impressive places. Check out a map of this ride...I've done it before (except for the drive through Denver).

Ride safe.

 

I've been in the Colorado Springs area for about a year now, haven't been too far west on the bike yet (but have in the Jeep). That being said, while Pike's Peak is a cool place to see, more than half the times we've gone there (in the cage), the peak has been closed due to high winds. And they don't publish that info except at the gate where you pay because the status changes rapidly throughout any given day.

I'd plan to go West from Denver over Mt Evans (even higher ride than PP) and follow Whisker's route. I'm going to the four corners rally over labor day weekend, so I'm taking something close to the southern route he described from Durango back towards the Springs area.

As one other rider recommended, there's plenty of cool things to do in Manitou Springs and you won't regret a quick ride through Garden of the Gods, too, on the way back.

Regarding the weather - you have to plan for 30-40F same-day temperature swings on a ride like this. And the rain will be impossible to forecast - but you will get wet at some point, even if most of the storms are relatively short. And yes, it may snow in September through some of the peaks.