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Route 66 : Chicago to LA

“Just take my way that’s the highway that’s the best” Bobby Troup 1946.

When the road was originally designated in 1926, it started in Chicago, Ilinois and ended in Los Angeles, California, but was extended in 1936 to Santa Monica on the coast. It was officially removed from the US Highway System in 1985.

End of Historic Route 66 Sign -Image by Andrzej from Pixabay
End of Historic Route 66

Many sections of the route have since been preserved as Historic Route 66. The impact of the National Highways bypassing small towns like those of the original Route 66, form the basis of the Pixar Film “Cars”.

Historic Route 66 Sign - Image by HUNTER16 from Pixabay

Planning a driving holiday this year, then there could be no better choice than driving down Route 66 from Chicago to Los Angeles linking hundreds of rural communities along the way.

Although the original route was declassified many years ago with careful planning its possible to drive along most of it.  There are some excellent Historic Route 66 Maps and Guides (*AD) available to help you plan your journey.

Route 66  
Copyright Linnaea Mallette
Route 66

Most people drive the Route 66 East to West, so all the rental cars end up in the West.  You can save up to 30% on the cost of your car rental by travelling from West to East plus you get the benefit of a shorter flight back to the UK.

The original Route 66passes through eight states and nearly 2,500 miles of diverse landscapes and historic communities. Travellers can explore classic roadside attractions such as vintage neon signs, restored diners, quirky museums, and well-preserved motels that capture the spirit of mid-20th century American travel.

Cities like St. Louis, Tulsa, Albuquerque, and Flagstaff each offer unique glimpses into the cultural and economic history that made Route 66 famous.

Due to its length of the highlights of a Route 66 journey is the remarkable variety of scenery along the way. The route crosses the rolling plains of the Midwest, the wide-open prairies of Oklahoma and Texas, the dramatic mesas of New Mexico, and the striking deserts of Arizona and California.

Cadillac Ranch - Image by Rosy / Bad Homburg / Germany from Pixabay
Cadillac Ranch

Popular stops include Cadillac Ranch near Amarillo, the Painted Desert and Petrified Forest National Park in Arizona, and the charming town of Williams, known as the gateway to the Grand Canyon. Each region offers a distinct blend of natural beauty, local traditions, and historic landmarks that make the journey as memorable as the destination.

Painted Desert Arizona - Image by blairelizabethbwn0 from Pixabay
Painted Desert

A trip along Route 66 is not just a drive across the country; it is a nostalgic exploration of American culture, history, and the enduring appeal of the open road.

Best Times to Go

  • May – June: Please temperature and long daylight hours.
  • September – October: Less crowded with excellent weather.
  • Avoid July – August for the sections in the Arizona and California deserts, where temperatures can become dangerously high.

Check out our:

14 Day Route 66 Road Trip Itinerary

7 Day Route 66 Road Trip Itinerary

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Aspen Colorado USA

Aspen, Colorado

There are many reasons to choose to visit Aspen, but for most of us, we will visit to take advantage of the many recreational opportunities on offer all year round as an excuse to travel there.

Top of the list has to be the skiing. Aspen boasts four mountains that are a paradise for both skiers and snowboarders. It is the perfect place for skiers of all standards from the beginner right through to the most experienced, offering a wide array of slopes, as well as plenty of runs through expert-only terrain. In fact Aspen has hosted the Winter X games on numerous occasions.

Skiing - Aspen, Colorado
Skiing – Aspen, Colorado

For fans of other winter activities you will be able to ice skate, and cross-country ski. In the summer Aspen attracts many hikers and cyclists. However there are plenty of opportunities for fishing, golf, horseback riding, and rock climbing. If you are into aerial sports then paragliding in one of the most beautiful parts of the world has got to be a major attraction.

Maroon Bells - RyanFSpack
Maroon Bells

Top of the list of sites are the Maroon Bells, a combination of a reflective lake, Maroon Peak and North Maroon Peak. Located 10 miles west of Aspen in a glacial valley the 14,000 foot peaks provide a dramatic backdrop to your hike or drive in the area.

Finally in Summer Aspen is home to the Aspen Music Festival. Founded in 1949, the Aspen Music Festival and School is regarded as one of the top classical music festivals in the United States, noted both for its concert programming and its musical training of mostly young-adult music students.