Route 66 Highlights: One Road, Many Possibilities…

The long-gone Route 66 originally started in Chicago, Illinois and ended in Santa Monica, California stretching a total of 2,448 miles (3,940 km). It opened for business on November 11, 1926 and withstood several re-routings before its eventual decline and final decommissioning on June 27, 1985. There had been several efforts to preserve the historic roadway, associations and historic registries, until President Bill Clinton signed the National Route 66 Preservation Bill in 1999. The National Park Service provides a travel itinerary and maps that detail the 85% of the route that is still drivable. So, pack up you rucksack and gas up the classic car, it’s time for an All-American road trip – which should include the ten Route 66 highlights we’ve listed below!

Route 66 Raceway

route-66-raceway-logoThe most important part of your trip is how you’re going to get from point A to point B. National Historic Route 66 Federation suggests renting a car from one of the major car rental agencies. You can pick it up at your starting point and drop it off whenever you’re sick of driving. For the hardcore traveler, they have tips for veteran bikers’ road tripping on their trusty Harley’s. You can always bring your bed with you and drive a camper. Before you set out, test your ride at the Route 66 Raceway! They have all kinds of events from drag races to demolition derbies (perhaps not in a rental car) and national level races.

Lou Mitchell’s

lou-mitchells-restaurantOnce you’ve got your wheels, you’ve got to fill-up YOU! Stop in to Lou Mitchell’s for some of their “world’s finest coffee” and delicious donuts. Perfect road fuel! The restaurant was founded in 1923, just a few years before the opening of Route 66. Over 85 years later, they are still pumping out some of Chicago’s best diner food. Of course, you’ll have your own personal tastes, but some of the favourites on the menu include perfectly cooked omelettes and mouthwatering Belgian waffles. Don’t forget that they also do carry-out, just in case you can’t resist carrying on your Route 66 journey as soon as possible, but the atmosphere inside is part of the experience that makes this one of the most enduring Route 66 highlights…

Old Chain of Rocks Bridge

old-chain-of-rocks-bridgeOn your way into Missouri, be sure to go over the Old Chain of Rocks Bridge into St. Louis. You wouldn’t forget it anytime soon, especially after making the 30 degree turn midway across this mile-long bridge that stretches the mighty Mississippi River. The bridge was originally supposed to be straight but riverboat men protested that navigating the bridge piers and water intake towers would prove to be extremely treacherous. The engineers conceded and the bent bridge was opened to traffic in July 1929. The bridge was closed in 1968 but reopened to pedestrian and bike traffic in 1999. So stretch your legs and walk part of the “original” Route 66.

Meramec Caverns

meramec-cavernsGo explore Missouri’s “buried treasure” at Meramec Caverns in Stanton, Missouri, where infamous outlaw Jesse James hid out from the sheriff. Missouri is known as the Cave State; it is home to more than 6,000 surveyed caves and the Meremec Caverns are undoubtedly the most famous, attracting around 150,000 visitors every year. For a fee, you can go on a guided tour of the caves with one of their trained rangers. Also, stop by the Meramac State Park for some outdoor fun. There you can enjoy swimming, fishing, rafting and canoeing in the Meramec River. From March through to October, you can also participate in an hour long zip-line experience.

Blue Whale of Catoosa

blue-whale-of-catoosaYou can’t do Route 66 without stopping at some crazy kitschy roadside attraction. That’s where the Blue Whale of Catoosa fits in. One of the most recognizable icons of historic Route 66 sits on the edge of pond in Catoosa, OK. The whale is the product of Hugh S. Davis’ imagination. It took two years to build and the unpainted whale began attracting people the summer of 1972. They would fling themselves off his tail, slide down his fins, and poke around his insides. It went into disrepair and closed in 1988. The city restored the whale and painted him his current blue color. It has been enjoyed by locals and travelers since it’s reopening in 1997.

U-Drop Inn

u-drop-innIf you’ve ever watched Pixar’s movie Cars, you will recognize the U-Drop Inn in Shamrock, Texas. Built in 1936, after the completion of US Highways 66 and 83 many new businesses began to shot up almost out of the bare ground, like the tower sprouting out of the top of the service station at the U-Drop Inn. It was originally a full-service gas station and roadside inn that could service your car and you. It is now home to the Shamrock Chamber of Commerce & Economic Development Corporation. In 2003-2004, the building was restored to its original sparkle and was adapted into a museum, visitors’ center, gift shop, and city’s Chamber of Commerce.

Cadillac Ranch

cadillac-ranchThey sprout out of the ground like daisies in the Texas desert. A line of brightly painted Cadillacs with their noses in the sand. Known as the Cadillac Ranch, it is a public art installation and sculpture west of Amarillo, Texas and your next must-see stop along Route 66. It was created by a hippie art group that called themselves The Ant Farm and funded by a silent partner, local millionaire Stanley Marsh 3. It was erected in 1974 in a wheat field and was moved to its current location in 1997 to place it further from the limits of the growing town. The group collected 10 used and junk Cadillacs, ranging in model years from 1948 to 1963. The installation is meant to represent the “Golden Age” of American automobiles. Over the years the cars have collected layers of graffiti left by visitors to the ranch. Will you leave your mark on the ranch?

City of Tucumcari

tucumcari-postcardThe City of Tucumcari has been a popular stop along Route 66 for decades. With a population of 5,363, it is the largest town between Amarillo, Texas and Albuquerque, New Mexico. The town is mentioned in many pop and folk songs and was the backdrop for many Clint Eastwood movies in the late 50s into the 60s. It is one of the highway’s best-preserved towns, filled with curio shops and diners dating back to the road’s glory days from the 1930s to the 1950s. There are many billboards along the highway beckoning you to stay in “TUCUMCARI TONITE!”. So why not stop off at the blue neon lit Blue Swallow Motel, believed to be the oldest continually operating motel on the Route. It is sold as “a unique experience out of another time.” Very unique, that it is.

Teepee Hotels

wigwam-motelTwo out of America’s three surviving renovated concrete teepee hotels are along Route 66. The first you will come to is in Holbrook, NM and the second in San Bernardino, CA. Both are still functioning motels with all the normal amenities, expect these come with bragging rights that you stayed in a teepee on your journey westward.  This stop was also inspiration for the movie Cars, expect for those cars stayed in giant traffic cones at the Cozy Cone Motel. It should be mentioned that these hotels are now somewhat of a tourist trap, so many choose to visit simply for the photo opportunity, before heading on to Flagstaff for a night’s sleep.

Santa Monica Pier

santa-monica-pier-signEnd your journey at the Santa Monica Pier in Santa Monica, California. The pier was originally constructed in 1909 to solve a sewage dispose problem; this disposal method was thankfully discontinued in the 1920s. In the 1960s, it was seen as an aging eyesore. A community of artists and activists fought for its preservation and in 1975 voters pass “Proposition 1” – an initiative which preserves the Pier forever. Today it is a national icon and it has become a premiere event venue. You can enjoy the pier year-round. Ride the merry-go-round, visit the aquarium, or fly high at the trapeze school. Then ponder your journey down Route 66, which you have now managed to complete!


So, if you are on a gap year in the USA, Route 66 is perhaps one of the most memorable and exciting trips you could possibly do! It might take a bit of time, but the journey really does live up to all the hype. If you don’t have the time though, why not check out some of the other things to do in the USA?

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