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Route 66 is probably the most imaginative route there is in the United States. Route 66 was established in 1926 and officially removed from the US Highway System in 1985, but keeps being popular among people wanting to travel as much of the original route by car or motorcycle. Route 66 basically was not just one simple road between Chicago and Los Angeles. Instead, constant changes over the years meant that routes and total length constantly changed. But during the years, Route 66 at least was recognisable as a road that you could actually follow all the way towards the west coast of the USA.
Nowadays, it is much more difficult to travel this route. Parts of the road are now designated a National Scenic Byway or are named Historic Route 66, and are perfect for those who want to combine a more modern roadtrip to the USA with some historical background by following as many parts of the original Route 66.
The traditional start of Route 66 is near downtown Chicago by the train station. It is possible to eat at a restaurant that claims to be the first (or last) restaurant on the road depending on which way you're going. One of the longest and most popular stretches travels between Kingman and Seligman in Arizona, making a loop northwards from Interstate 40 and passing several smaller villages. Great vintage signs, some diners and motels can still be found on this stretch of historic Route 66.
The original Route 66 runs from near the train station in Chicago, Illinois, through the states of Missouri, Kansas (5 miles!), Oklahoma, Texas, New Mexico, Arizona and California, before ending in Los Angeles. Later on, the official ending was removed from downtown LA to Santa Monica at the Pacific coast.
It goes beyond the scope of this article to mention all cities along the way, but some of the main ones are:
Although Route 66 is a major sight itself, there are plenty of places to visit along the way. Many of the cities and towns have at least things to keep the Route 66 dream alive, but there are loads of sights and activities in other places as well. For more information, it is best to read the articles about the specific places and states.
In general, the western half of Route 66 is the best regarding landscapes, nature, open skies and far vistas and it also has the most quirky places to stay and eat (see below). If you can only do parts of Route 66, make sure that you travel this part, for example between Amarillo and Los Angeles.
The main gateways are the Chicago O'Hare International Airport and Los Angeles International Airport. Other options include Chicago Midway International Airport and Lambert-St. Louis International Airport, but you can also fly to airports relatively near places along Route 66, like San Diego International Airport, Phoenix Sky Harbor International Airport, Las Vegas McCarran International Airport, Kansas City International Airport and Dallas/Fort Worth International Airport.
Both Chicago and Los Angeles have train stations and Amtrak operates trains on a number of routes. Some of them also run between these two places. There are also connections to/from Los Angeles along almost the entire Pacific coastline between San Diego and Seattle/Vancouver, and to/from Chicago there are connections west towards New York and south towards New Orleans, with many places in between. Visit the website for details about prices and schedules.
A good system of Interstates and Highways connects places along Route 66 with the rest of the country.
Most of the places along Route 66 have connections by bus. Your best bet is to check Greyhound, which has the most extensive network, some of the routes in addition to Amtrak trains.
Although both Chicago and Los Angeles are at or near the water, not much useful connections are available. There are no ferry services to/from Chicago, and the ones to/from Los Angeles are to the Channel Islands and Santa Catalina island, about an hour out of the coastline and leaving from places like Long Beach or Ventura.
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Of course, as Route 66 is a road itself, the only way to get around basically is by car or motorcycle. You might choose to take the bicycle of course, but although it's surely a healthy way of travelling, this is not what Route 66 is all about. If you can, hire a motorcycle or, even better, an old American vintage car from the 1950's or 1960's. Otherwise, a relatively new convertible is another decent option, for example a Corvette or Mustang. But let's face it: any car will can handle the easy tarmac roads, so renting one with the major car rental companies like Hertz, Thrifty, Avis, Alamo, Budget, National, Dollar or Enterprise will suffice. Carefully check all the details about renting a car of course, especially all the extra costs regarding insurance, extra drivers and most importantly one-way dropoff costs. Usually these dropoff costs are cheapest with National, about US$250 regardless of the miles travelled. If you travel all the way from Chicago to Los Angeles, this saves you lots of money.
There are dozens of cities and towns along Route 66, so it's best to check the respective places for a full list of places. There are, however, a few that really stand out and are totally in line with what Route 66 is all about these days: vintage style, old cars, history and quirky places. A few examples are:
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