66 Road-Schild auf grünen Feldern in Illinois

Route 66 Highway: the Eastern States

Discover the best route 66 roadside attractions

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The world-renowned US Route 66 highway is popular among car enthusiasts and American history and culture fans alike. The eastern half of a Route 66 road trip will take you through four states, and past many exciting attractions. Here are some top tips for the ultimate driving adventure.

Chain of Rocks Bridge, Chain Madison

A few hours from its starting point in Chicago, Route 66 takes you to Madison, Illinois, home to the historic Chain of Rocks Bridge. Spanning the Mississippi River, the bridge links Madison with the city of St. Louis, Missouri, on the opposite bank. Constructed in 1929, the one-mile (1.6-kilometer) bridge takes its name from a stretch of rocky rapids on the Mississippi, notoriously difficult to navigate by boat.

The road bridge, which was part of the old Route 66, is known for its striking bend in the middle of the structure. The crossing was replaced with a new bridge in 1966, but is no longer open to vehicles. However, it’s still popular with walkers and cyclists, so be sure to take advantage of the nearby parking lot and stroll across the famous river.

Die alte Chain of Rocks-Brücke, einst Teil der Route 66.
Die alte Chain of Rocks-Brücke reicht über den Mississippi hinaus

Gateway Arch, St. Louis

Having crossed the Mississippi, you’ll find yourself in the city of St. Louis as you join Route 66 in Missouri. No visit to St. Louis is complete without taking in America’s tallest manmade monument – the Gateway Arch. Designed by Finnish-American architect Eero Saarinen, and rising an impressive 630 feet (192 meters) above you, the Gateway Arch celebrates the vision of President Thomas Jefferson, and the pioneers who helped expand the United States by populating its western regions. St. Louis played a key role in the rapid westward expansion that occurred in the early 1800s. The city became a key trading point for fur traders and grew rapidly after the War of 1812, when huge numbers of pioneers traveled west in search of a better life.

The monument is located in Gateway Arch National Park, where you can find ample places to park, and a free museum. Bold visitors, who don’t mind heights, can take a 45-60 minute tram tour, which takes you to the very top of the monument to enjoy magnificent views to the east and west.

Beleuchteter Gateway Arch über St. Louis
Der atemberaubende Gateway Arch dominiert die Skyline von St. Louis.

66 Drive-In Theater, Carthage

After crossing the state of Missouri from east to west, Route 66 passes the town of Carthage, near the Kansas border. Carthage is home to the 66 Drive-in theater, one of the few historic drive-in theaters still operating along the old 66 highway.

American drive-in theaters had their heyday in the 1940s and 50s, and the vast majority have now closed. Thankfully, a few of the drive-ins are still in operation, including the 66 Drive-in. Built in 1949, it still boasts many of its original structural elements, including neon signs and a screen with a classic 4:3 aspect ratio, and operates during the spring and summer months on a first-come, first-served basis.

Galena: Cars Movie on Route 66

While only passing through Kansas for a brief 13 miles (21 kilometers), Route 66 takes you past the small town of Galena, which is the inspiration for Disney’s popular animated Cars movie. Route 66 drivers today can pull up to the old Kan-O-Tex service station, originally restored by four local women, and now known as “Cars on the Route” in homage to the movie.

In addition to fueling up on snacks and souvenirs made by local artists, you can check out some of the old vehicles that inspired the movie, including the mining boom truck on which the popular “Tow Mater” character is based.

Blue Whale, Catoosa

As Route 66 winds its way across the state of Oklahoma, you’ll pass through the sleepy town of Catoosa, on the outskirts of the city of Tulsa. But zipping through the town without stopping would be a mistake, as you’d miss one of the most well-loved attractions along Route 66 – the Blue Whale.

This giant replica of the world’s largest mammal stands 20 feet (6 meters) high and 80 feet (24 meters) long, and is located in a pond to the east of downtown Catoosa. Built by local man Hugh Davis as a wedding anniversary present for his wife, who was fascinated by the animals, the Blue Whale took two years to complete and was eventually finished in 1972. Today, the attraction is owned and operated by Davis’ daughter, and is a must-see for any road tripper on the Route 66 highway.

Route 66 highway sign on green fields of Illinois

Find the best route 66 roadside attractions

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