
Route 66 Start To Finish – I will be 55 in March of next year and have started planning the trip of a lifetime which is taking historic Route 66 across America with my better half ( Pam ). I have already bought the maps and SD card for Tom Tom. I know it’s over 12 months away but this is a once in a lifetime trip and I want to get it right. I also want to take my time and enjoy every phase from the planning to the actual trip itself. We don’t like guided tours and prefer to do our own so it’s just the two of us.
This is the bike we are going to take which is a 2006 roaring eagle super classic electra glider that has done 30,000 miles and would imagine there could be a few more on the clock by the time we are done.
Route 66 Start To Finish
We are going to be away for 7 weeks and have already found that it will be cheaper to take our own bike rather than renting one there. Our initial plan is to send the bike to New York have a few days sightseeing before we go to Niagra Falls then head down to Chicago to reach the starting point of the historic route 66 which will end in Los Angeles.
The Highlights Of Route 66
We are going to go off the road to reach other sights like the Mississippi River, Monument valley, Grand Canyon and many other interesting places that I will fill in later with the help of Google Earth and books I have bought.
I have found a great website called www.historic66.com which has a lot of information, it also has a GPS section and I have managed to download the entire route onto my Tom Tom which consists of 19 itineraries with all the waypoints to keep us on track track The only thing is, I won’t know if it works until we’re in America. It seems to have loaded fine and I’m sure it will be fine. This will have saved me weeks of studying maps and creating my own waypoints and I can now focus on some of the detours we will take along the way.
Time marches on and it will be here before we know it so I’m starting to set things in stone. We now have a start and end date with our route mapped out. Yesterday I ordered the transfer of the bike and our plane tickets. I have decided to go with a company called James cargo based in Manchester. I can return the bike for them to come in a crate that they take pictures of during the process. The bike will be flown directly to EWR Airport in New Jersey ready for us to pick up. The return journey will be by ship from Los Angeles to Kent, then straight back to Manchester which will take 6 to 9 weeks.
Next week I’m going to get our New York hotel booked (this will be the only thing I’ll pre-book for the holiday) I’ll also look into grouping our medical and bike insurance with breakdown cover.
Best Attractions On Route 66 You Must Visit
I recently had a problem with the bike which to make a long story short ended up with a new engine costing £6,000.00. On the plus side, I turned the old machine into a wonderful timepiece with a little help from eBay.
Below is our proposed route which is constantly changing. People have suggested going no more than 200 miles a day so you get plenty of opportunities to stop and explore. Our average will be about 150 miles a day.
I have bought a few maps and for the planning stage I have found Harley Davidson Historic Route 66 very useful for the first stages as it shows the whole route in 5 separate sections, which includes points of interest and also a Harley dealership (which could be handy if we need ) this has enabled me to reinforce the places to have a night stop. I would then cross-check this with Tom Tom’s route planner to confirm the distance between stops, and also see if that would give us time to see any points of interest along the way. I had gotten away with putting these in Tom Tom as favorites but since you are only limited to about 20, I then started making itineraries but since I am only in the planning stage things kept changing and it was getting very confusing , so I have decided to make an excel spreadsheet with all the addresses and zip codes
All the overnight stops, points of interest along the way, I’ve also added waypoints to keep us on the 66. I’ll post them as itineraries when I’m completely satisfied. I said early on I downloaded route plans for Route 66. I have now decided to delete these and use my own route with the help of “Jim Ross and Jerry McClanahan’s route 66 pull out maps” and google earth which is a great program and you can experience almost everything the holiday without leaving the UK.
How Long Does It Take To Drive Route 66?
I’m 99.9% done with the planning and will avoid the temptation to put the details into Tom Tom until a few weeks in advance.
Below is an excerpt from my excel spreadsheet that I will insert into Tom Toms itinerary and then create waypoints and stops, the black text is used for overnight stops with an address for a potential hotel, the blue text is for destinations, and the red text is for points of interest places or stops.
We don’t want to come to America and find out we can’t fit all our luggage on the bike, so we’ve both been making our own lists and in the next few weeks we’ll see if it all fits on the bike. Next time we will get cheap suite cases and transfer the luggage to them so we can check the weight (I bet we will be over the limit) if so I know I can carry some of the heavy stuff like waterproofs and helmets in the bike when I go that to James cargo. I said cheap bags as these will be thrown away when we get to New York and buy two more in Los Angeles for the return trip.
21 days to go and time is ticking and very quickly I’m already getting the butterflies. We have done our trial pack today and I have to say Pam has done a really good job, this has left us plenty of empty space so we can buy goodies to bring home. We will, however, use the empty space with old dirty socks, baggy socks and tops and drop them on the way to save on laundry. The bike has been serviced and is booked with James Cargo on the 27th to be ready to fly to America on the 6th of September.
The Ultimate Route 66 Road Trip Guide
Safety could be an issue when we are visually inspecting and the bike is left alone as most of the top luggage is easily accessible, so I bought some waterproof material from eBay and made a cover that we will use as and when we feel like it. necessary.
The bike has been returned by James cargo and I must say I was impressed with the installation and sure it will be well packed and looked after ready for the flight next Friday. The gas tank is empty, the battery is disconnected and the tires are partially deflated before they are placed in the coffin.
That’s about it for my planning which is left to enjoy the trip starting on Sunday. If you click on the newer posts tab on the bottom left it should take you to my next post which I will update daily if time allows. From flashy neon to roadside kitsch, here’s everything you need to know about the Mother Road, complete with interactive maps.

Route 66 is the ultimate embodiment of the road and its greatest promises: freedom and serenity, kitsch and living history, and a case study of how Americans have moved and reproduced. You can certainly travel east on Route 66 (in fact, we highly recommend it), but there’s no denying the symbolic power of at least one westbound trip along the stretch of asphalt.
Joplin, Route 66 Missouri
Our brand new Route 66 book will help you find every classic, quirky and fun stop along the Mother Road.
Ready to get started? Don’t leave home without your trusty Route 66 map. It’s a good idea to bring a paper map of Route 66 as a backup if you don’t have cell phone reception. But the tour operator is going to be your best friend on the trip, with
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