SpeechlessTwo Rivers, WI

Sign sketch by Chandler O'Leary

There really are no words for this one—except that ever since I saw this sign, I’ve found ways to work in the term “ho-made” to as many things as possible. Comedic gold.

As an aside, I didn’t sketch it, but just a few blocks away is a bait shop that sells wine and spirits. Read that last sentence again, and let it sink in. The Tailor and I wanted to buy a bottle of wine for our host that evening, so we asked a local where we might find something. She gave us directions, but apologized for not being able to give more information than that. “I can never remember the name of the place, because I just call it ‘Wine & Worms,” she said.

Oh, yes, this is my kinda town.

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Towering guiltChandelier Drive-Thru Tree, Leggett, CA

Drive-Thru Tree sketch by Chandler O'Leary

You know, if you think about it, a place that lets you pay money to drive your car through a hole cut into a centuries-old living redwood tree is kind of the perfect illustration of the bad side of American culture.

The first time I was (literally) in this neck of the woods, the guilt won out, and I passed it by. Then, earlier this year, the side of me that plans trips around things like Wall Drug hijacked my internal monologue, screaming, “You HAVE to stop! This is EXACTLY the sort of thing you love! They already drilled the tunnel, so you might as well!” And so I gave in. And you know what?

I loved every second of it.

Sorry, redwood tree. I’ll go plant a sapling as penance.

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Lush, eh?Blind River, Ontario

Lupines sketch by Chandler O'Leary

A couple of summers ago, the Tailor and I took a cross-country road trip along the Trans-Canada Highway. For hundreds and hundreds of miles, the roadsides were dotted with bright pink, blue and purple lupines. It felt like all of Canada was one big, bright bouquet.

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Have a seatPenland School of Crafts, Penland, NC

Adirondack chairs sketch by Chandler O'Leary

I don’t know if there’s something about the Blue Ridge Mountains, or about the pace of life in the mountains of the South, or what. But whenever I had a free moment during my visit to Penland last summer, I had an irresistible urge to sit back in a deck chair and stare out into the hills.

Rocking chairs sketch by Chandler O'Leary

Good thing there was ample opportunity. North Carolina is chock full of comfy, inviting chairs and gorgeous views—as soon as I saw that, I knew we were going to get along famously.

Penland School of Crafts sketch by Chandler O'Leary

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Sea shantiesSalmon Beach, Tacoma, WA

Salmon Beach sketch by Chandler O'Leary

Salmon Beach might just be the best-kept secret on Puget Sound. I’d been dying to do a sketch there, and I finally got my chance a few weeks ago. The entire area is private property, and only residents and their guests are allowed. But my friend Ethan lives there, so I asked if he’d be willing to give me a tour. I had no idea that I was in for one of the best adventures I’ve had since I moved to Washington.

Salmon Beach sketch by Chandler O'Leary

Salmon Beach is a neighborhood of 80-odd homes arranged in single file along the shoreline of the Tacoma Narrows. There are only two ways to get there: by boat or by descending (on foot) several hundred wooden steps leading down from the parking lot at the top of the cliff.

Salmon Beach sketch by Chandler O'Leary

The way down is dizzying, and the return trip is a heckuva workout. I’d imagine that if I lived here, I’d learn quickly not to forget my keys in the car.

Salmon Beach sketch by Chandler O'Leary

At the bottom is what feels like a time warp, or some sort of alternate dimension. The residents of Salmon Beach live in their own world, secluded but also open and extremely welcoming. Friendly household pets of every stripe wander around the boardwalk (they don’t run away, because where would they go?), and people greeted me with stories and tips on the best drawing spots.

I was so excited to share their world for an afternoon. Big thanks to Ethan for the grand tour, and to everyone I met that day—it feels so good to be in on the secret.

Salmon Beach sketch by Chandler O'Leary

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Giddy up, IchabodCornish-Winsor bridge, Cornish, NH

Covered bridge sketch by Chandler O'Leary

I have a thing for covered bridges—and thankfully, many other people do, too. That means the communities that possess these relics work hard to preserve them, and I’m grateful that there are still covered bridges for me to sketch. And each one is so wonderfully sketch-able, because they’re all so different.

The Cornish-Winsor Bridge, which straddles the New Hampshire-Vermont border, is one of my all-time favorites. And not just because of the two-dolla fine notice, either (though if any Sleepy Hollow ghouls chase me I’m stayin’ on my hoss). For me, the best part is how absurdly long the span is.

Have you ever crossed a covered bridge? Which one is your favorite?

Covered bridge sketch by Chandler O'Leary

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Banana split for my babyFranklin Fountain, Philadelphia, PA

Franklin Fountain sketch by Chandler O'Leary

I got lucky with this place. I happened to glance at the New York Times a couple of days before we left for Philly to visit our friend Gilles, and stumbled upon a glowing review. When we got there, it was Gilles’ birthday and blazing hot outside: hello, ice cream parlor!

Franklin Fountain sketch by Chandler O'Leary

And hello, best ice cream of my life. It’s been two years since I was here, and I can still taste the maple syrup. If you find yourself in Philadelphia this summer, grab some cash (they don’t take plastic), get in line (it’s packed), and get ready for a dish of heaven.

Franklin Fountain sketch by Chandler O'Leary

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Four cornersVarious locations in New Mexico, Arizona and Utah

Four Corners sketch by Chandler O'Leary

The Tailor and I make for an odd pair on a road trip. I’m likely to put enormous thought into the road tunes, to cue up the exact perfect song to play as we pass through certain landscapes (I am also usually the only one who notices or cares, no matter who’s with me on a trip). He, on the other hand, is likely to have one half of his mind in the present moment, and the other half somewhere in the Annals of Random History.

For instance, on this day, I was all wrapped up in how the weather seemed to shift with the music, when the Tailor turned to me and said, “Did you know that considering today’s date and our current time zone, the Titanic was sinking precisely one hundred years ago?!?”

So of course I had to add that to the sketchbook. Doesn’t the desert remind everyone of maritime disasters?

Four Corners sketch by Chandler O'Leary

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Where the Heck?Wall Drug, South Dakota

Wall Drug billboard sketches by Chandler O'Leary

I was born 50 miles west of Wall Drug. True story. I think, therefore, that my undying love of roadside attractions is imprinted on the genetic level.

Even if you don’t have this place in your DNA, it’s pretty hard not to be curious about something hawked by a hundred billboards as you drive through the back of beyond.

Wall Drug sketch by Chandler O'Leary

Then again, if you hate jackalopes, it’s best to turn back now. If, like me, you adore them—well, you’ve come to the right place.

Wall Drug sketch by Chandler O'Leary

The souvenirs ain’t cheap, but you can fill your travel-weary belly for next to nothing. There’s the five-cent coffee (not bad!), the free ice water (alkaline!), the ho-made doughnuts (pretty dang good!), and various hot-meal items (absolutely terrible!).

Before you leave, be sure to see the creepy animatronic Gold Rush puppets sing “North! To Alaska.” (Sorry, no sketch of that. I was too scared.) And when you hit the road again, you’ll be able to look back and see the 80-foot dinosaur standing vigil, waiting for your return.

So if you go—send me a postcard, will you?

Wall Drug sketch by Chandler O'Leary

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