10 Classic U.S. Road Trips

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10 Classic U.S. Road Trips

Whether by horse, wagon, jalopy, motorcycle, bicycle, caravan or minivan, road trips have been a bullet on many travel bucket lists and often considered a rite of passage throughout America’s history. Early expeditions, like Lewis and Clark’s Corps of Discovery and the Oregon Trail, were about finding new land or the promise of a better life. Other trips, like those that inspired Jack Kerouac’s On the Road, William Least Heat-Moon’s Blue Highways: A Journey Into America, and John Steinbeck’s Travels with Charley were about the journey into one’s self.

Crossing the country (or even just a state) by road is not about getting to the destination, it is the destination. These 10 road trips are inspired by the ever-changing scenery they offer along the way and by the great expeditions of the past. They are by no means untraveled roads, but in the age of air travel, these routes are worth the journey.

1. Route 66
Illinois to California

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Photo via Flickr / Vicente Villamón

There is no stretch of road more closely associated with Americana than Route 66. Dubbed the “Main Street of America,” 66 takes you from Chicago to Santa Monica and covers more than 2,000 miles when traveled in its entirety across Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. It opened in 1926 and continues to take drivers through the heart of America. The miles are marked by a diversified itinerary of attractions including national parks (Grand Canyon National Park and the Mojave National Preserve), architectural landmarks (Willis Tower and the Gateway Arch), roadside oddities (the world’s largest ketchup bottle, covered wagon, rocking chair), countless billboards, motels, and no shortage of greasy diners.

2. Pacific Coast Highway
California to Washington

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Photo via Flickr / Rian Castillo

The Pacific Coast Highway (U.S. Route 101) is a winding coastal stretch of road from Los Angeles to Olympia, Washington. Driving these miles (around 1,500 or more) offers ocean views and cliff-hugging curves. While the California portion of this West Coast road trip (typically Los Angeles to San Francisco) is the most popular, adding Washington and Oregon includes additional stops in Portland and Seattle and attractions like Olympic National Park and the Oregon Dune National Recreation Area. The California stretch includes drives through Redwood National and State Parks, the Golden Gate Bridge, Big Sur, as well as the 700-feet high Bixby Bridge.

3. Great River Road
Minnesota to Louisiana

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Photo via Flickr / Dave Herholz

This more than 2,000-mile road trip through the middle of America, which has been designated a National Scenic Byway, is guided by the Mississippi River and takes you north to south along a series of local roads and highways. From the river’s trickling headwaters at Lake Itasca in Minnesota to the delta in Louisiana, you’ll cover 10 states in total (Minnesota, Wisconsin, Iowa, Illinois, Missouri, Kentucky, Tennessee, Arkansas, Mississippi and Louisiana) as you chase the bends and riverboats of the Big Muddy. Window views include flat plains, rolling hills, dairy farms, massive limestone bluffs, swamps and plenty of feathered and furred wildlife. Be sure to stop at St. Louis’s Gateway Arch, indulge in some Blues music and barbecue in Memphis, and binge on beignets in New Orlean’s French Quarter.

4. Overseas Highway
Miami to Key West, Florida

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Photo via Flickr / Karen Bleier/AFP/Getty Images

Connecting mainland Florida with Key West, this road trip takes you on the final 150 or so miles of U.S. Route 1, more commonly called the Overseas Highway. You’ll be rewarded with 360-degree ocean views as you islet hop your way over down more than 150 miles and over more than 40 bridges on your way to Key West. Start in Miami where there are enough beaches, museums and Cuban food to fill a few days before hitting the road. As you set out toward Key West, you’ll pass through Key Largo, dubbed the dive capital of the world. The Keys are home to the only living coral reef in the continental United States, so be sure to visit the John Pennekamp Coral Reef State Park where glass-bottom boat, snorkeling and scuba diving tours are available. Dolphins, osprey, manatees and even bald eagles are among the wildlife you will likely spot as you continue further south to Key West. Once you’ve arrived, snorkel and sunbathe to your heart’s content in the southernmost city in the continental United States.

5. The Oregon Trail
Missouri to Oregon

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Photo via Flickr / Matt Turner

Follow the Oregon Trail on this westward road trip without the risk of losing a wagon wheel or succumbing to dysentery. The more than 2,000-mile route starts in Independence, Missouri just like the thousands of pioneers who embarked on this journey in the 19th century. Before heading out, visit the National Frontier Trails Museum for perspective and inspiration. As you make your way across Missouri, Kansas, Nebraska, Wyoming, Idaho and Oregon, you’ll be surrounded by plains and desert landscapes, many of which remain untouched by modern civilization. Keep an eye out for the tombstones of those who perished on the Oregon Trail, as well as the wagon wheel ruts they left behind.

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