Boston Crawling: History, Brew, and all Things Boston

A little over two years ago Bobby Heaney found himself in a field he was not particularly fond of. He had a strong sense of wanderlust throughout his life and reevaluated what he loved about travel. Often times the best experiences revolved around beer, history, and meeting great people. He combined these experiences to create Boston Crawling. A company that guides groups throughout Boston to experience some of the rich history of the city with a local brew in hand.

Boston Crawling gives your employees the chance to get out of the office, learn some exciting history, and try out some beer totally unique to the city of Boston. These bars are not the obvious choice for tourists and locals alike. Be sure to take note because they will keep you coming back for that unique brew.

Boston Crawling Highlights

Pub crawling is a favorable way to enjoy a few exclusive beers of the area. Boston Crawling tours are sure to please everyone from the seasoned local to the fresh faced intern. The history your group will be learning is the not always taught in schools or books. So you will be sure to leave with new knowledge of this historic city!

  • A history lesson on Boston you were never taught! Tour guides will teach you about the important role beer has had in our nation’s history. As well as some stories about your favorite brews.
  • Boston is the home of Sam Adams and Harpoon, so you know you are going to be treated to some quality beer. Try exclusive Boston flavors or home brews by the pubs you will be visiting.
  • Some employees not a fan of beer? Try out one of the packages which allows employees to order wine or mixed drinks.
  • The Boston Crawling Tour is not just for tourists. You may live in the city and be considered a local but this history is hidden, just like the pubs.
  • No need to rent a car or figure out transportation to and from each location. You will be visiting four pubs within 2 blocks! All are close walking distance.
  • Boston Crawling does not provide food. However, if you would like to have food available at any of the locations they would be happy to set something up so participants can munch while they drink.
  • Listening to keynote speakers or trust falls may not be for everyone when it comes to team building. Some people prefer to just grab a beer and get to know one another in a pub setting. Go for something a little bit different to bond every employee.
  • Tours can be hosted for 10 to 150 people. Larger groups will be broken up into smaller sizes and rotated. This way everyone gets a chance to order and enjoy a drink!
  • Tours can last between 2 hours and 15 minutes up to 2 hours and 45 minutes. This depends on the size of the group and if food is requested.
  • Is it suggested that groups book 30 days in advance. However, not a problem if on a shorter notice.

Boston Crawling Package Options

Learn about the different package options offered with Boston Crawling to choose the one that fits best.

  1. Happy Hour Package – A guided Pub Crawl along Boston’s Freedom Trail. The package includes four local craft beers at each location. Priced at $55 per person.
  2. Dry Run Package – Includes the guided Pub Crawl along Boston’s Freedom trail. It does not include drinks but is a perfect option for those corporate groups looking to put all drinks on one tab. This also gives people the option of ordering wine or mixed drinks at each location.

Boston Crawling Photos

It is always a good time with Boston Crawling. Learn the history of Boston walking to and from each pub. Enjoy a pint surrounded by that warmth American bar vibe with some of your closest coworkers!

 

Interview with Bobby, Owner and Chief Crawling Officer of Boston Crawling

Listen to my interview with Bobby, the owner and chief crawling officer of Boston Crawling. We talk about how he came up with Boston Crawling, the kind of history you will learn about on a tour, and what makes these bars so unique.

Interview Transcript

Kristen: Hi, this is Kristen from Team Building Hero. Today we are interviewing Boston Crawling. I have Bobby who is the owner and the chief crawling officer. Thank you so much for joining me Bobby.

Bobby: Yea, thanks for having me.

Kristen: Awesome, so first can you just tell us how Boston Crawling got started?

Bobby: Sure, Boston Crawling is actually 2 years and 1 day old today. Our birthday was yesterday. It started because I am actually a recovering attorney. I practiced law for about 6 years before I started in Boston Crawling. It just wasn’t for me. I knew after one semester of law school that I didn’t want to be a lawyer, but I am not a quitter! So I stayed with it, kept practicing, thinking it might get better. It got to the point where I was doing so bad that I didn’t want to go to sleep at night cause I didn’t want to wake up in the morning. I knew I had to change course.

I started with the question that they always tell you to start with but no one ever does and that is ‘what do I love?’ I wrote that at the top of a piece of paper and I realized that some of my happiest memories are of always traveling. I had Wanderlust in my younger days. I backpacked through Europe by myself. Studied in Australia …studied in Prague. I have driven from New York to San Francisco and back. I worked out in Yellowstone for a little bit. I have always had that kind of bug. I started to think, ‘what did I always like about that?’ I really loved meeting people from around the world. I loved learning history when I was traveling. Not the typical textbook history, like the nitty gritty dirty stuff that they teach on the tours. Then, of course, I always loved drinking the local beer when I was traveling. So I combined ….

-call dropped-

(2:40)
Bobby: So I combined those three things. Meeting people from around the world, hidden history, and good local craft beer, into a historic pub crawl company called Boston Crawling. That is how we were born.

Kristen: Fantastic, that is actually a really cool story. I am a bit of a recovering public accountant. I totally understand trying a new field and doing something a little bit maybe more adventurous. That is totally awesome. Can you walk us through a corporate event with Boston Crawling?

Bobby: Yea. So corporate events, we can basically do any size. Anywhere from 10 to — we have a booking for October for 150 people. What that entails is they will all meet at a central location. A historic spot here in Boston and then we take you to 4 different historic bars in Boston. All along the way we are giving a history tour. We try to keep it half socializing / half history. So you are not being lectured for too long. You get a chance to hang out with your fellow team members but you also get to learn about the city of Boston and some fun and cool stories that we offer.

Each bar has its own historic significance as well. We recommend good local beers that you cannot find anywhere else. The larger the group the more likely we’re going to have to split into multiple tours. So we can basically crawl up to 30 people on one tour as long as we have two guides. But say you have more than that, for example that 150 group. We are splitting it into multiple groups of 30. With guides starting at different bars and just going in a circle with everyone finishing at the same bar. But it is a good fun way to get your team out, get them interacting with each other but also to see the city of Boston a little bit.

Kristen: Awesome, so if you have a company you are doing an event for and the company is from Boston, they live there, do you go to hidden bars that they have never heard of before?

Bobby: Yea, so the bars we go to all have history and yet none of them are really tourist traps. So whether you are from Boston or not from Boston these bars are not likely ones that you are going to normally go into. We do try to find the hidden gems here in Boston. The history that we offer is often the stuff that is left out of an 8th grade social studies class. So a lot of Bostonians will say to us after, “Wow, I never knew any of that.” That is always a cool feeling.

Kristen: Is it history about the beer or how each place got started?

Bobby: Yea, so outside of each bar we offer history of the bar itself and what the bars background is. Once we are inside our little history presentation is on everything from how beer affected the landing at Plymouth Rock up to the start of the Revolution. We cover such significant events like the Boston massacre. We’ve discussed not only Sam Adams the beer but Sam Adams the person. So it is a little bit of everything.

Kristen: Awesome. So all these bars you go to, are they locally brewed or is there like a special aspect to them?

Bobby: So beer in the bars, some bars offer house brew made by Sam Adams or Harpoon brewery here in Boston. For the ones that don’t, we offer ones that Sam Adams and Harpoon only sell in Boston. While they might not be specific to that bar you are not going to find them from outside of the city.

Kristen: So what is included in these tours? Is there drinks included? Can you do like a lunch or maybe a dinner with them?

Bobby: We have two different standard options. The first is the happy hour package. That includes 4 beers, one at each bar we go to. So it comes out to 2 pints, a 12 ounce and a 10 ounce. That will cost $60 for a private group. That includes gratuity so you don’t have to worry about tipping the guide. That includes $5 per head in gratuity. Otherwise we offer a dry run reservation. That includes no beer and you would be responsible for directly buying the drinks from the bar. That is $35 also including gratuity. So a lot of corporate groups what they will do is they will buy the dry run and then just open one tab at each bar. Because it is hard to determine whether people are beer drinkers, wine drinkers, if they like harder alcohol, or if they don’t want to drink four beers at all. So usually we recommend for a private group to do the dry run option. We don’t normally include food in our standard pricing. However with corporate groups they often would like food. We can arrange with the bars to have the food ready. They can prepay for that or they can pay at the bar themselves. We would just need to speak with whoever is in charge of booking. In terms of food they want, how many bars they want to have food. Things like that.

Kristen: With these corporate events, so say a company wants to do a Boston Crawling event, if they want to implement team building skills or do more bonding is that something that you offer? Or is that something you encourage corporations to come up with on their own? Is there a way to do that?

Bobby: Yea, so at each bar we have plenty of time for socializing. We ourselves don’t offer any sort of team building activities besides the history and of course getting people beer, that seems to bring people together. But in terms of having the amount of time or something like that they can certainly do that in the bars themselves. Normally our tours run about 2 hours and 15 minutes. Giving us around a half hour to 45 minutes per bar. But again, with corporate groups we can vary the start time, vary the length and work to accommodate the group for exactly what they want.

Kristen: Ok, and do you drive to each of these locations or are they like walking distance?

Bobby: Yup, all of our bars are really close to each other. They are in the historic vanhull district of Boston. So the entire walking portion is literally 2 blocks. So we hit 4 bars in 2 blocks. We like to keep the bars as close together as possible. So we make the bars the experience, not necessarily the walking and also because we want to accommodate anyone who might need some help with traveling from spot to spot.

Kristen: Fantastic, so can you tell us a little bit about the price ranges and what is included in the price? I am sorry… we already covered that actually…yea I think actually you answered all of my questions. How far ahead should people book in advance?

Bobby: Yea, so our weekends book up pretty quickly. I would say, especially for a corporate group, you want to try to give 30 days notice. There are a lot of times where they want to start at a different time. We normally crawl at 3:00 and 7:00 everyday. But for private groups they may want to crawl at 5:00, they want to start at noon. We can arrange any of that as long as we have enough of a heads up. I would say 30 days is plenty of time, but we are always willing to take bookings when they come.

Kristen: Ok, and how long are these events?

Bobby: Yea, about 2 hours and 15 minutes. A larger group may run a little bit longer, like 2 and a half , 2 hours and 45, just cause you got to get everyone from bar to bar. Make sure everyone gets their drinks. But again if they order food I would say on the longer side that theirs too, would be about 2 hours and 45 minutes.

Kristen: Ok, great. I think I actually went through all my questions. That was great. Do you have anything else that you would like to add about Boston Crawling?

Bobby: Yea, I would like to say that we are a fun alternative way to see the city. Because we get you your drinks and we get you your history. People find themselves debating whether they want to do drinks or a history tour. We are the perfect compromise for both. You will definitely have enough drinks to have a good time, but enough history to say that you learned something while you were here in Boston.

Kristen: Awesome, well thank you so much for your time. That was a lot of great information. Yea we are all set.

Bobby: Great, thanks Kristen. If you need anything else just let me know.

Kristen: Will do, thanks. You are listening to Team Building Hero. I am Kristen and that was Bobby the owner of Boston Crawling. Thanks

Bobby: Cheers!

Boston Crawling Reviews

Boston Crawling is an enjoyable way try some unique local brews you won’t be able to get anywhere else. Even if history is not your thing, learn some of the nitty gritty stories that your history teacher probably left out.

“Absolute awesome time. Great history lesson along with excellent beer. I will do this again with friends just so they can experience it. I would highly recommend this as a pub crawl if you’re looking to try one. Great tour guide(s).” – Josh Jacob, Facebook

“As someone who is native to the area, I found this really insightful. Not only was the tour guide was really knowledgeable about the history of Boston, but he had a perspective that was original and witty. If you want to have a text book tour, go somewhere else. If you want to know about the REAL history of Boston, while enjoying a Boston beer, take this tour!” – Daniela S., Yelp

“Entertained both out of towners and locals and everyone has a great time. Garrison shared some great stories of history and several debates spiraled off as we shared some of the local brews. Highly recommend as a night out doing something fun and different”. – Stephen W., Trip Advisor