Bob Heaney: World Traveler and Boston Historic Bar Crawl Champ

bob heaney

Infected with what seemed like an incurable case of wanderlust from a young age, Bob Heaney, founder of Boston Crawling historic pub crawls, has seen more of the world than many people will in their lifetime. Studying abroad in Australia, backpacking through over 21 cities by himself in Europe and working in Yellowstone National Park, Heaney was always hungry to meet new people, see new places and keep pushing on to the next adventure.

It wasn’t until he came to Boston for law school that he finally found a city that could tame his wanderlust. After graduating from New England School of Law and discovering the field wasn’t for him, this Long Island native decided he was going to devote his life to the three things he is most passionate about: meeting new people, drinking good craft beer and learning hidden history. Boston, as it turned out, was the perfect city for this.

You describe yourself as having “wanderlust.” How did you first discover this about yourself? What drove your desire to go out and see the world?

I’ve had wanderlust since I was a kid. I remembered if you asked all the other kids what they wanted to do when they grow up, they would say “doctor, lawyer..” and I was like, I just want to go to college. I want to get away.

I grew up in a nice, safe neighborhood, and all my friends were happy to live there. I was actually home last weekend and everyone was still there. That’s just not for me. I wanted to go out and see everything before I settled on a place. I wanted to make sure I was happy. I didn’t want to settle on a place just because I was born there. I wanted to see the world.

How did these experiences change your worldview?

What did Mark Twain say? Travel is the death of bigotry? I might be confusing that line, but basically, the more you travel, the more you learn, the broader your worldview becomes. And it’s fascinating learning about other cultures, different people. And it’s fun. And that’s part of the reason why I started Boston Crawling. I knew I couldn’t keep traveling for the rest of my life, so I brought those travelers, those like-minded people to myself.

What made you go to law school? What made you realize it wasn’t for you?

I was terrified about the real world, and instead of figuring that out, I took the easy way out and took out more student loans and went back to school… That’s what happens when you let fear drive you. You make mistakes.

Law in general is an adversarial system…  It’s a constant competition, which means you always have to prove that you are right and the other person is wrong. I found that translates to even having a beer with people after class… And dealing with that attitude of knowing it all and trying to constantly trying to be right didn’t fit with me.

What made you decide to start a bar crawl? Why was Boston such a good fit for the crawls you wanted to do?

I was partly inspired by Shark Tank. I saw all these people doing the jobs they love, and I said, you know what, I should do something I am passionate about. I might dive more into the work instead of just getting by.

Boston is great for a lot of different reasons. First of all, we are obviously the birthplace of America. We have so much history, and we’re also head of the craft beer revolution. We have a ton of terrific craft breweries and cider houses, so there’s a ton of great beer to discuss and drink along the way. And it’s also a walking city… so people of any capacity, any age can walk and crawl with us.

What types of people do you meet on these crawls? What do you hope they take away from your crawls?

We have met everyone, CEOs of Fortune 500 companies to a kid I went to grammar school with. We didn’t even know until the third bar that we grew up and went to grammar school together. So you really meet people from all over the world. I’ve seen license plates from all 50 states at this point, and many, many different countries, as far as China and Australia.

A lot of the time, we get feedback from our crawlers, “we had such a good time, we ended up going out to dinner with everyone else on the crawl,” and those always make me smile that people are getting the same experience I had while traveling through Europe

Boston Crawling bar crawlers

Heaney (right) and his bar crawlers


Would you describe this as a good conclusion to your world travels?

I don’t want to call it a conclusion, because I never want to be done traveling and experiencing everything… I knew traveling wasn’t going to be as easy anymore, so why not bring those people to me? And it’s great. I get to meet people from everywhere, every walk of life… It’s just really fun and really fulfilling.

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