September
 

If it was me Id go in September, October can get cold and snow. You will miss much of the heat in AZ and still stay out of most of the bad weather.

I don't think simplyshaker wants to go to parks and the like. He as many europeans hear and dream of the "Mother road" and riding a big fat HD. Its His dream and wants to know how to prepare for the ride.

For the cold weather get some heated vest, pants, cold weather gloves, boots and wool socks. For the rain some rain gear. All of this can be had in most any bike shop at the start of the trip. Failing that Wallmart will have gear to get you by. Wallmart may also have a dry bag to store your things in, some bungies and you will be good to go.

If you going to use leathers gets them treated with water repellent many leather shops will sell the stuff you need or the Harley store will have some. It wont stop you getting wet but it will help and save the leather.

The weather and elevation change are part of the ride the challenge. Its the crap that gos wrong on a ride that makes the ride memorable. The wind, the rain, the cold, the heat, the bad food its all there and when you overcome all this you come across something that makes all worth it. Seeing the plains that go on for days, the rockies come out of the grate plains, dropping in to the heat, riding out of the desert to the mountins, seeing lights of LA, the Pacific at sunset. Its the trip you will remember not the road.

As far as not having room for the gear have the dealer set you up with some saddle bags AND a bag for the back rest like a T-bag or get a dry bag from a sports store. You may want to have a wind shield put on the bike if dose not come with one, they look funny but are grate. The two of you may have to do with out some of the things you want. But will be dry and happer.

IMO Route 66 is seriously overated. I rode across the US in 2002 and again last summer (3 months, 15,000 miles) and there are a gazillion better places to see. OK my experience of Route 66 in 2002 was about 100 miles of it - and just to get the sticker!

Get a National Parks season ticket which will allow you into as many of the breath taking National Parks as you can fit in.

Leathers? Personally I would never, ever wear leather in the US during their summers as it's far, far too hot. FirstGear mesh jacket, H-G Toureg light coloured trousers, Olympia gel gloves (thin) and a white Arai open face helmet. Should you ever ride across Death Valley (118f then I twice crossed it) or Arizona (almost too hot to ride during the day), you'll discover I'm right.

Route 66 just HAS to be done on a Harley. Oh dear. My Pan is the (almost) perfect long distance touring bike for me. If image, bandanas, attitude and tyre kicking is for you.......so be it.

I saw a t-shirt for sale on the Isle of Man this summer. It said "There are thousands of Harleys on the road.....the rest made it home!"

IMHO, Route 66 is the most over rated stretch of highway in existence.

If you are flying into Chicago and wish to go for a memorable ride, get on your bikes and ride due west to Sturgis, South Dakota and the Black Hills. From here, go further west to Yellowstone National Park. Also check out Glacier National Park. Go south into Colorado. Then into Utah. Finish up in San Diego, California.
This trip will be 100 (more like 100,000) times more memorable than bland Route 66.

If you're riding Harleys, do your best not to fall into the mindset of "better to suffer than look uncool". It seems like most Harley riders do their best to dress in a manner so they look like pirates, even during inclement weather.
Leather is fairly useless in the rain, as it wicks up water after time, and riders stay wet & cold. Rain gear keeps a person comfortable & dry. Full face helmets fend off the wind/cold/rain. Don't forget slipovers for hands & feet or some sort of waterproof wear. Wet boots can take days to dry if its the only footwear one has.

Riding hundreds of miles in the rain is a trying experience. It is even more miserable when one is cold & wet.

The chances of encountering rain when traveling from east to west are great. The chances diminish as one enters the arid climate of the southwest.

Yellowstone was the biggest waste of time and effort I have ever done. Overrated, overcrowded, overtouted, and overpriced. We saw One bison, one raven, some elk and some geese. There is no real scenery, just brown grass most of the time. The traffic was so bad you were at 10-15 mph most of the time and where there was something to see, the cars were piled up 6 deep. The hotels charged no less than 110 a night and there were no rooms in West Yellowstone. We rode another 50 miles southeast before getting a room at 97 bucks. The next day we said the hell with it and rode back to Oregon, covering 740 miles before 8:00 pm and paid 42.49 for a room in Bend. Would have made it sooner but there was a fire just east of Burns and had to wait for our turn to travel on the one open lane the firefighters were keeping open.

Save your money and go to Utah and the canyons.

Sidetrip to the Ozarks
 

Down around where Route 66 cuts through SW Missouri, drop down for a few days in the Ozark Mountains. Good riding, good scenery, lots of little backwoods places. Life slows down there a tad. Get off the main highways (although you can do the Pig Hwy in Arkansas - Route 23).

Everyone else posting here is talking about Arizona and California - lots of Route 66 before you get out in that wasteland.

all true but
 

Yes most every one I have ever met that ran 66 has said the same things I did it once, lived in AZ so ran it there to NM a few times on it.

BUT he want to ride 66 on a hog its his dream.

We need to suport his dream not try to kill it. I want to go to South America its my dream Im going to go. The roads there are more or less like ones I can find in the USA. No one here will try to talk me out of it, Its why I read pages here.

Now If he dose go then wants to see other things or bags some of the areas along 66 we can all jump in and help him out.

And pretty well all of it is deadly, deadly boring. As you and others have pointed out, you don´t have to get far from Route 66 to see amazing scenery, but sticking to the Mother Road itself is daft. It´s 70 years past its sell-by date.

I´d add my vote to those suggesting linking Sturgis and the National Parks. Yellowstone is wonderful out of the main summer season (best to spend more than a day, though :() , and from there you can cut down to Utah and Canyonlands and Arches and Monument Valley.

There´s no question of trying to kill the guy´s dream. On the contrary, it makes sense to point out that Route 66 is actually a very long and very boring stretch of road, but that almost the entire length of it is a few miles to a few hundred miles away from some of the most staggeringly beautiful scenery in the world. IMO, Sturgis to Yellowstone to Jackson and on south into Utah is a far more interesting route. Chicago to LA (I´d pick SF, personally, and catch Death Valley, Mammoth and Yosemite, too) is a hell of a ride. But to spend days in Oklahama is a bit much for anybody to be asked to take!

Al

maby he like it
 

Yes but it the dream. Look what people drive today isnt the old 66 any way. It was once a dirt road. Then it was a string of roads. There have been many revisions to that road over the years. but some of that road still remains.

The road is much like the USA. The old USA the cool USA it is still there you gust got to look a bit past the the new shinny mask.

The reason people talk about CA to NM on 66 is that is what most Europeans want to go see. It the places they see on the movies its the Americana they want to see. Its the post world war 2 happy America. The look and feel that USA had.

To tell the truth no I do not like the road its in bad shape and all the shops along it sell the same boring junk. But its not the road people go for its the dream.

Get a few books on the road like Amazon.com: Route 66: The Mother Road: Books: Michael Wallis
This may help with what to see where it is and how to get there. Know that 66 has been moved more than a few times and has been fragmented so a map and guide book will help out a lot.


As far as places to go The USA federal park system is impressive and you will see some of it on 66. like painted dessert, petrified forest, the Grand Canyon is not to far off dont remember but theres one in Oklahama and a museum there to.

Sturgis to Utah can be just as bad as 66 and far more loaded up with gray hairs driving RV with as much SQ. feet as my house. Add in there are pass over 7,000 to 10,000 feet and you may well be geting in to snow at the time you are planing for the trip.

I think there is a happy medium here. I used to work and live in the heart of the Navajo Indian Reservation. We lived two hours from Flagstaff, Arizona, 2 hours from Parker, Arizona, and 2 hours from Monument Valley. The old Route 66 was parallel to Interstate 40 in this area, but the real beauty lay north of that road. I think that taking the road for the sake of taking it, is a romantic, and realistic thing to do. However, when one starts getting near worthwhile sights, then one should see them by taking detours, such as going from Gallup, New Mexico, through the Navajo Nation, to Monument Valley, into Utah, and back down to Flagstaff, Arizona.