The Art of the Pub Crawl, How to Feast on Live Crawfish & the Mission to Keep Austin Weird

Word on the Street with Chris Herndon of The Guild

In each edition of “Word on the Street,” we interview a Guide to learn about their Sidewalk and some of their best travel stories.

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Meet Chris Herndon, the co-founder of The Guild, a boutique short-term rental and hotel rolled into one. He divulges on his favorite speakeasy, belting Bon Jovi in the Big Easy and spending the afternoon hanging with Bill Clinton.

1. You and The Guild just published a few Sidewalks that provide the local’s take on the best of Austin. One of your most popular walks is, A Hipstertastic East 6th Cocktail & Crafty Crawl. What’s that Sidewalk about?

“Cocktail and Crafty” is a shout out to the “Keep Austin Weird” culture. Downtown has become commercialized with its chain restaurants and corporate vibe. South Congress started unique, but has become a little pedestrian.

East 6th is one of the few places in Austin where there are more locals than tourists. It still has a hip, authentic aura to it, and a little grit and grunge. That vibe plus the craft cocktails make it  “Austin-y.”

2. Do you have a favorite place along the crawl?

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I gotta say, I love the Milonga Room. This place is completely Prohibition Era. It’s in the basement of the Buenos Aires Cafe and looks like a Roaring 20s speakeasy. Dimly lit, 7-foot tall ceilings, candles, lots of red velvet furniture. It’s super space-constrained; “intimate,” let’s call it.

3. What do you hope people get out of going on “Cocktail & Crafty”?

I hope they go to some places they wouldn’t go to otherwise. I hope they understand the story arc that the bars provide as a whole. There is a method to the sequence, there is a diversity in the experience, there is an art to the walk.

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This is for our guests who want to explore the neighborhood. It’s also for the 150 new residents who move to Austin everyday who want to get immersed in this city. And it’s for the folks who have lived here for years and are looking to really impress with these staples of East 6th.

4. “Cocktail & Crafty” is more than a pub crawl. There really is an exploration of a neighborhood told through its bars.

Exactly. The thing I like about this Sidewalk is that it’s a curated adventure with a lot of personality and humanity to it. It better mimics the experience of having a local friend who picks you up and takes care of you when you travel somewhere new.

5. You travel a lot. If you could have anyone in history pick you up and take care of you, who would it be and where would you go?

Bill Clinton. And actually, I don’t care what city we’re in as long as it is somewhere social. Maybe a bar, maybe a cafe. He is one of the most personable storytellers ever.

I just want to sit at a table with him and watch people come up to shake hands and ask him questions. There is real joy in sitting and socializing, meeting people you wouldn’t expect to meet and shooting the breeze.

6. Where have you traveled that really surprised you?

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When I was younger, I went on a 6-week backpacking trip to Europe with a few buddies. It’s one of those things you only do until a certain age. We met up with a friend in France who was heading to Aix-en-Provence for 3 days. Aside from seeing lavender fields, I had no idea what you do there. It turns out, Aix-en-Provence was one of the most memorable places on the trip.

It over-delivered across every dimension. The town was amazing with its Old World charm - the vibrancy and amazing food. The diversity of terrain was incredible; we went on a 3-hour hike in the mountains outside of Aix that took us from dry grasslands to dense forest.

I loved it so much that after I got married, my wife and I went on holiday to Europe and I made sure that Aix was one of our stops. I got to show her all my favorite spots. She is a sommelier, so she was smitten with the vintage bottle shops. Meanwhile, that gave me some time to pop into a local pub. The bar was electric - packed with people slugging pints, smoking heaters, and watching the Arsenal - Chelsea match. I ended up meeting some guys that actually still keep in touch today.

7. What is the craziest thing you’ve ever eaten?

There was a place on Main Street in Park City with crawdads that they would bread and pan fry. But the catch is, they would still be alive when you put them in your mouth. They were delicious. Kind of like soft shell crab, but light and crumbly. And clearly still alive. I haven’t seen that on the menu anywhere since.

8. What’s a place you are embarrassed to admit that you love?

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Bourbon Street, New Orleans. It’s very cliche, very touristy. And people like to talk down about that place. But everybody is happy, there is no pretense to it, the drinks are cheap and you don’t feel lame when you’re singing Bon Jovi at the top of your lungs. Nothing is out of bounds. No one is going to look down at you for doing anything because something worse is probably going on next door.

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If you're planning a trip to Austin, check out The Guild. It's one part eclectic home, one part boutique hotel, and one part hipster friend who will take you to the best spots in town. Each property has a dedicated Sidewalk, so you can feel like a local as you explore at your speed and style.

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Jason Donahue, Co-Founder & CEO

Interview has been condensed and edited.

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