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Route 66 Road Trip: Your All American Guide

As with most things, when it comes to road trip planning, I’m a classic kind of guy. So when it comes to seeing this great nation from sea to shining sea, I do the classic All-American road trip—Route 66. Running from Chicago to Santa Monica, the Mother Road, the Will Rogers Memorial Highway, the Main Street of America—there’s no more classic American road trip than Route 66. Not only will you get to see the U.S., but you’ll get to see the real U.S., from sea to shining sea.

Flagstaff, AZ

Santa Monica to Flagstaff is a bit of a hike, but when you get to Flagstaff, you’re going to marvel at just how great this little city is. In fact, Route 66 is largely a tour of forgotten and overlooked American cities. But Flagstaff is a gem, every bit the emerald beauty that cities you’d be more likely to consider green are, such as Portland, OR. So, if you’re a fan of outdoor activities and the musty smell of damp woods, you’ll love it here. And, if you’re an indoor kitty, Flagstaff boasts everything from dive bars to craft brewpubs. Whatever you do—and this applies to every city on this list—mingle and meet the locals. It’s just not an American road trip otherwise.

Amarillo, TX

As dusty as Flagstaff is green, Amarillo sits on the Texas Panhandle, not far from Lubbock for any fans of Waylon Jennings and Buddy Holly who wish to make the trip down. It’s perhaps the most stridently blue-collar city on the list. Get ready to meet roughnecks when you take the town at night. A flat part of a flat state, there’s not much on the horizon, but you can see forever. Don’t forget to hit up the Cadillac Ranch, a collection of decaying old Cadillacs buried halfway in the Texas dirt. Plenty of hip coffee shops and dive bar delights for meeting the locals.

Oklahoma City, OK

Few cities in modern history have grown up quite as quickly as Oklahoma City. This means that just about everything in the city is new, but if you dig around, you can find some older gems lurking around, including the city’s famous “Barmuda Triangle,” the best three dive bars in the city. Edna’s was featured in a Toby Keith video while the Hilo Club across the street displays original Googie architecture and signage. The National Cowboy & Western Heritage Museum is also there, providing you with a rare opportunity to see everything you need to know about this era of American history.

St. Louis, MO

Sitting right on the Mississippi River, St. Louis is a city that’s on the grow. What was until recently a blighted urban landscape has given rise to more brew pubs and hipster dive bars than you can shake a stick at. The Arch is there, of course, as is the Anheuser-Busch mother brewery, each a classic American icon in their own right. On the way, you’ll get lush views of the Ozark mountains coming and going.

Boston, MA

Route 66 ends in Chicago, but once you’ve made it that far, you might as well continue all the way out to the other coast. Boston, MA is one of America’s oldest cities and you can enjoy the "civilized life" there — cannabis has been legal since 2017. The museums in Boston are without compare to anywhere else in the United States, save for our nation’s capital, which is an equally worthy place to end your road trip.

An American road trip allows you the opportunity to see the country in a way other forms of travel simply do not. While you shouldn’t skimp on the sights, make sure you get out there and meet some of the people while you’re at it—they’re what make America great.

Banner Image: Stewart Leiwakabessy / GettyImages


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