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By USA specialist Rob

It spans 2,400 miles, crosses eight states and three time zones, and enlists you for at least three weeks. The epitome of American driving holidays, Route 66 takes you east to west, from Chicago to Santa Monica, Los Angeles, tracing the development of the pioneering country. The original road no longer exists unbroken, but as a road trip the route holds strong. It will take you through small-town America and past some of the most obscure attractions in the country.

Starting the road trip in Chicago

Chicago is the starting point for most Route 66 tours. The city warrants a few nights’ stay to take in its live music venues and museums, the sculptures of Millennium Park and the sandy beaches of Lake Michigan. In a city famous for pizza, I also rate Pizzeria Uno, Chicago’s first deep-dish pizza restaurant.

The city’s also known as the birthplace of skyscrapers. The world’s first was constructed here in 1885, just ten storeys high. Since then, the number has grown to 121, and their design and height have become increasingly impressive.

Architecture river cruise

One of the best ways to appreciate Chicago’s skyline is from the Chicago River. If you’re visiting between May and September, we can arrange for you to join an hour-long boat cruise that focuses on the city’s architecture. Your on-board guide is likely to be an architecture graduate or student, equipped to tell you all about the design, construction and history of the key buildings.

Among the most notable are the 141 m (462 ft) neo-Gothic Tribune Tower, the Wrigley Building, whose style was influenced by Spanish colonial revival and French Renaissance architecture, and the Willis (Sears) Tower, at 442 m (1,450 ft) the tallest building in the world for 25 years.

As interesting, in my mind, was seeing how these skyscrapers slot in alongside older brick buildings, some of which have stood since the city’s beginnings.

You won’t need a car to travel around Chicago as it’s an easy city to explore on foot and by public transport. Once you’re ready to begin the drive, you can pick up your hire car downtown before making your way to the start of the route, which is just around the corner.

Driving from Chicago to Springfield, Illinois

From Chicago, it takes two and a half hours through prairies and farmland to reach Springfield, the capital of Illinois.

Despite its proximity to Chicago, Springfield feels a world away, its red-brick architecture a contrast to the Windy City’s high rises.

Lincoln Home National Historic Site

Springfield was the hometown of Abraham Lincoln in the 17 years leading up to his presidency. You can visit the house where he lived, an attractive wooden building with large shuttered windows. Now a National Historic Site, it has been restored to reflect the era in which Lincoln lived there with his family.

Due to the house’s modest size, you can only look around on a ranger-led tour. From the kitchen and living area to the upstairs bedrooms, each room is furnished with items used by Lincoln in his day-to-day life. Your guide will point out the desk at which Lincoln wrote his memoirs, his bed, and the large mahogany table where he ate his meals.

Afterwards, I suggest strolling around the surrounding four blocks, where 12 buildings have also been restored to their 1860 heyday. It really helps to paint a picture of the Springfield Lincoln knew. Exhibits tell you about the past residents, most of whom would have known and interacted with Lincoln.

Springfield or Branson?

From St Louis you have two choices. The first is to continue along Route 66 to Springfield, Missouri, noted for its classic cars that line the streets outside old-fashioned motels. While the city isn’t immediately alluring, I found that it grew on me as I took time to discover its hidden depths. With few other visitors, the city’s residents were keen to speak to me about their hometown, and I got the feeling that Springfield is beginning to embrace its Route 66 heritage.

Alternatively, take a short detour through the Ozark Mountains to the city of Branson. This all-American, slightly eccentric town sits within America’s Bible Belt so has a heavy Christian influence. Along with visiting the town’s theme parks, I suggest attending one of the shows that are held by multiple generations of Mormon families. From playing country music to performing magic tricks, they feel a bit like a variety show, and are usually very patriotic.

Driving to Oklahoma City

The countryside is flat and green as you make your way to Oklahoma City. Four hours from Branson, this compact metropolis is a highlight of Route 66 for me. It’s partly for its food, which is an eclectic mix of American South Cajun dishes and Mexican fare.

Oklahoma City Dodgers baseball match

During your stay, we can arrange for you to watch the Oklahoma City Dodgers. The minor-league baseball team’s home is the Chickasaw Bricktown Ballpark, right in the heart of Bricktown.

Unlike the big-name teams, like the Yankees, where much of the crowd are visitors, almost everyone here is a local supporter. It means you get to cheer shoulder-to-shoulder with true fans.

Baseball matches tend to last for several hours, so it’s up to you if you just want a taster or to stay for the whole duration. I suggest getting there in time to experience the national anthem before the game, when the whole stadium erupts into song.

Throughout the match, hot dog and popcorn sellers pace the stands, people clink bottles of beer and giant foam fingers are jabbed excitedly in the air.

Oklahoma City to Amarillo

Heading into the Texas Panhandle, the prairies of Oklahoma give way to a drier landscape. This five-hour section of the drive is a touch uninspiring and I recommend jumping on the freeway to eat up the miles.

The Interstate 40 (I-40) will take you to the next stop along Route 66 — Amarillo — of Tony Christie song fame. Although there’s not an awful lot to see here, it serves to break up the journey.

Visiting Cadillac Ranch

Ten miles outside Amarillo you’ll come across an unusual spectacle in a field adjacent to the road. Ten graffiti covered Cadillacs are buried nose first in the ground. What started as an art installation has become legendary along Route 66 and travellers, armed with their own spray cans, will leave a lasting reminder of their stop here.

Reaching the mid-way point on Route 66

A road sign in the tiny town of Adrian marks the road trip’s midpoint, before the route continues onto Santa Fe in New Mexico. Adrian is little more than one street and a quintessential small-town café, where a jukebox plays in the corner and American number plates hang on the walls. The café gift shop peddles halfway point souvenirs.

Santa Fe

Entering Santa Fe, you feel touched by the Mediterranean as you contrast the city with Amarillo. The Spanish-influenced old town square and Pueblo-style adobe architecture provide a setting that contrasts widely with the cities further east.

Albuquerque

The Sandia Mountains rise up around you as you drive from Santa Fe to Albuquerque, and if you drive through around sunset you’ll witness the light casting a red glow on the rocks.

Around an hour-and-a-half’s drive from Santa Fe, Albuquerque is a sprawling city sporting a number of Mexican and Spanish museums.

Albuquerque to Winslow

From Albuquerque, you travel into Arizona as you make your way to Winslow. En route, you pass through the Petrified Forest National Park, site of numerous palaeontological discoveries. The forest’s name derives from the fossilised wood found here. Throughout the park you’ll see normal-looking tree stumps, but with fossilised insides of inorganic material such as pyrite and opal.

Taking a detour to the Grand Canyon and Meteor Crater

While the Grand Canyon isn’t technically on Route 66, it’s worth a detour. The South Rim is the most accessible from the route and has the best viewpoints; although that does make it the most popular with visitors.

There are several walking trails, or you could take to the air on a helicopter tour, flying over the green Kaibab National Forest. As the trees disappear, the Grand Canyon opens up in front of you and you feel as if you’re going to fall off the edge of the world.

It takes around three hours to reach the South Rim from Winslow, a little longer if you make a stop at Meteor Crater just outside the town of Flagstaff. As the name suggests, the crater is a huge hole created by a meteorite that struck Earth almost 50,000 years ago. There are plenty of alien connotations with the site and you can only get within a certain distance of it, further fuelling speculation.

The Grand Canyon to Las Vegas

As with the Grand Canyon, Las Vegas isn’t considered part of the original Route 66. But, it’s a city you might be keen to experience at least once, and it’s close enough (five hours’ drive) to the canyon.

En route is Seligman, a classic Route 66 town of traditional motels, diners, shops and flashing neon signs. You can also make a stop at the Hoover Dam, just 40 miles outside the city, where you can join a ranger-led tour or explore under your own steam.

The dusty desert surrounds you as you make your way to Las Vegas, whose outline you can see on the horizon for miles as you approach.

Downtown Las Vegas food tour

Every visitor to Vegas flocks to the Strip, with its themed hotels and trademark casinos. But, in the Downtown district, you can experience a slightly more laid-back atmosphere that’s shared between visitors and locals.

In recent years, investors have seen this area’s potential and ploughed money into its regeneration. Independent shops and restaurants have opened up, and I felt an air of optimism and creativity as I strolled around.

You can join a small-group guided tour of Downtown, learning more about the area’s history and its plans for the future. At the same time, you’ll sample some of the signature dishes served at four of the best up-and-coming Downtown restaurants.

Among them is Therapy, an industrial-style restaurant where you can try contemporary comfort food such as chicken and red velvet waffle sliders. Far simpler than the name suggests, they’re a satisfying combination of buttermilk chicken on red breakfast waffles, served with punchy chipotle mayo.

We also called at 7th & Carson, which serves tapas-style dishes that fuse American classics with European and Middle Eastern cuisines. I sampled thick flatbread fresh from a wood-fired oven, dipping it into lightly spiced hummus, baba ganoush and yoghurt.

The tour ends with a visit to Container Park. Here, repurposed shipping containers house pop-up shops and restaurants. Live music often accompanies food served by some of the city’s newest chefs.

From Las Vegas to Santa Monica

It takes around four hours to drive from Las Vegas to the final destination on Route 66: Santa Monica in Los Angeles. You can break up the journey in Barstow, the last of the main points of interest along Route 66, where you can visit the Mother Road Museum. The museum displays a collection of memorabilia related to this historic route and is a fitting stop as you near the end of your drive.

The sign marking the end of Route 66 is located on Santa Monica’s pier. Nearby, The Last Stop Shop will award you a novelty certificate confirming you’ve completed the drive.

Private Cadillac tour of LA

After weeks of driving, it’s nice to end your trip as a passenger. On previous visits to LA, I’d found myself constantly stuck in traffic. But, on this three-hour tour, my driver knew exactly where to go to avoid congestion. Sitting in his polished burgundy 1970s Cadillac, the top down and the sun warming my face, we took in most of the city’s sights.

We passed through Bel Air and Beverly Hills, where my guide pointed out the mansions of celebrities. In Santa Monica, we glided along the waterfront with its glittering pier. And, driving through Hollywood, my guide regaled me with the history of LA’s film industry, interspersed with snippets of celebrity gossip.

Your driver will have lived in LA for years and can use their knowledge to tailor the route to your interests. I mentioned that I loved the TV show Modern Family and, lo and behold, I was driven past two houses that appear in the series.

Practicalities of driving Route 66

1. You need around three weeks to complete Route 66.
2. There is no perfect time to drive Route 66. Due to its sheer size, you’re likely to experience some adverse weather conditions, whatever the month. Oklahoma can see heavy downpours during April, while Las Vegas and the surrounding desert can reach temperatures of 45 degrees during the summer. Throughout the winter months, Chicago can prove particularly cold.
3. Road laws vary throughout the country, so check the speed limit when crossing into different states.
4. Filling the car up is an interesting experience in the USA, as different gas stations follow varying procedures. While one may expect you to swipe your card in store before filling up, another station will want you to hand your card over to the attendant beforehand, then return to pay once you’ve filled up.