Category: Highways and Byways

Somewhere to lean onGroom, TX

Route 66 sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here. I crossed Texas twice last year: once at its widest point (where we logged over… More

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Oklahoma PantheonArcadia, OK

Route 66 sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here. Last Friday’s post was a bit of a downer, I know. So today, as we… More

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Neon butterflyCentralia, WA

Highway 99 butterfly sign sketch by Chandler O'Leary

Speaking of the Chinese new year, I’m reminded of this beauty along old Highway 99. The restaurant is still very much alive, and its current owners are doing a great job of stewardship when it comes to their vintage neon. So this week I’m wishing them a happy and prosperous new year, too.

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Sunflower, sundownGalena, KS

Route 66 sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here. Logically, if you were to plan a trip from Chicago to Los Angeles, the shortest… More

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Farm to marketingPontiac, IL; Stanton, MO; Chandler, OK

Route 66 sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here. One of the most well-known—and most-hyped—tourist traps along Route 66 are the Meramec Caverns. Whether… More

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Ted’s tasty freezeSt. Louis, MO

Route 66 sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here. Our first day on Route 66 was bookended with pit stops at iconic Mother Road… More

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The first stopChicago, IL

Lou Mitchell's sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here. If you’re going to start Route 66 in Chicago, start your trip right with a… More

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Eastern terminusChicago, IL

Route 66 sketch by Chandler O'Leary

This post is part of an ongoing series called 66 Fridays, which explores the wonders of old Route 66. Click on the preceding “66 Fridays” link to view all posts in the series, or visit the initial overview post here. To help you keep your bearings in this 66 Fridays series, and to provide an… More

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Mother Road, mother lodeRoute 66

Route 66 sketch map by Chandler O'Leary

Last summer the Tailor and I spent a couple of weeks traveling every inch of old Route 66. And then I kept pretty quiet about it, because I just had no idea how to organize and share the sheer number of sketches and stories I came away with afterward. There really is no “long story… More

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The long viewMt. Tamalpais, CA

San Francisco Bay area sketch by Chandler O'Leary

On the morning I did this sketch, I was supposed to be sitting in a darkened lecture hall, listening to a bunch of scholars talk about art. But I just couldn’t do it. On a day like that, it seemed criminal to pass up such a beautiful place. So I jumped in the car and… More

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