Touring the City Runner Style

A few months ago I did a post about a great experience my husband and I had with City Running Tours in Boston.  It was the highlight of our trip and when we returned we started searching to see what other cities they had tours in.  We even tried to arrange a tour for our family back in Chicago.

Our Chicago branch of MDA Team Momentum trains together at least twice a week.  On Wednesdays we meet in the evening and the group usually tends to be a bit smaller.  During one of these runs an athlete mentioned that they were going to be away the following week on vacation and they were nervous about getting their mileage in for the week.  This is a legitimate concern, especially for people who are new to running.

My husband and I were trying to tell the athletes that the best part of being a runner is being able to throw on a pair of shoes and see a new city in ways that you couldn’t if you were just walking or riding a bike.  My husband started telling the team about our experience with City Running Tours and that he would check their website before heading out to any new city.  It was the perfect way to get a morning run in, see some spots in the city we wouldn’t have known to check out or at least how to get there, and it was just plain fun.

This is also a much better way to tour the city than on a bus or even a bike.  You are able to get to places a lot easier and don’t have to spend hours on and off of a bus or boat.  This tour manages to see just as much in a little over an hour as you would do in a half or full day on any other tour.

When I got home that night I told my husband that I wanted to reach out to the Chicago branch of City Running Tours.  As the coach for Team Momentum I am always trying to offer fun challenges to get our participants active and involved with the group.  I hoped that perhaps these guys might be able to offer something up for a challenge.  So I took a shot and e-mailed them.

I couldn’t believe it when I got an e-mail back almost immediately from their Chicago Manager, Blake Williams.  He was incredibly kind and mentioned the idea of doing a group run for our entire team.  I was psyched!  What a fun way for our team to get together for a group run, get some miles in, and have a chance to hang out together.  We are always running shoulder to shoulder and struggling to get long miles in, but we rarely get the chance to do something together that is a bit more social.  This was the perfect combination!

Last night a group of us gathered in the heart of Chicago at Universal Sole where we met our guides Blake and Aaron.  They were immediately warm and welcoming with both a sense of humor as well as a smart plan for our group’s safety.  After a brief description of where we would be running and what we would see, we were off on our 4 mile run.


Blake and Aaron took us on their new Streeterville Tour.  Our first stop was at the DuSable Bridge and the former site of Fort Dearborn.  It was here that a major massacre occurred during the War of 1812.  As you can see we were able to put our feet right where the former fort once stood and take in some beautiful relief sculptures.



Next we traveled to the Chicago Water Tower.  Built in the 1860’s and located right along the Magnificent Mile, this is one of the few historical buildings to have survived the Great Chicago Fire.


We swung by the Drake and learned about some of the fabulous people who have stayed there.  We stopped at the infamous John Hancock Building.  I still can’t get over the fact that some people take pleasure in racing up the steps of 94 stories of this building.  That almost sounds more painful than running a marathon!



I lost count of how many buildings we stopped by and learned that Oprah once had a residence inside.  And I am still amazed that some of the more fabulous areas of the city didn’t exist 100 years ago.  A lot of the city we know today was under water back then.

Our tour finished at the statue of George Streeter, the namesake of Streeterville.  I knew nothing of this guy but I am now ready to get my hands on some more information.  This guy tried to convince the city of Chicago that he owned a portion of the city that he had no right to. He spent decades in and out of jail while profiting from renting this land out.  He sounds both crazy and brilliant!


When our tour finally came to an end, right back at our starting point, we were all buzzing with energy from this fun evening run.  So we of course went around the corner to a local bar.  It was a great way to end a perfect run.  Our guide joined us and we continued to discuss the tour and the city a bit more in depth.  Most of our group commented on how they have either lived here all their lives or for a really long time and everyone agreed that they came away with a lot of great new knowledge about the city.

We couldn’t have picked a better way for our group to get together.  Not only did we get our Wednesday workout in, but we all had a great time together and left with some new insight on this beautiful city.  So many of our team members vowed that they will be checking the City Running tours website before they head out on their next vacation.

A special thanks to our awesome guides Blake and Aaron.  They were a wealth of knowledge but also super fun.  They cater to runners of all levels and are extremely accommodating.

City Running Tours can be found in 16 cities throughout the United States.  They offer various tours in each city and many will allow you to create a custom tour if you are so inclined.  Several of these run end at breweries or fun watering holes in local neighborhoods.  If you need to get some training mileage in while on vacation these guys can set something up for you on a more personal level.


Check them out at


17 thoughts on “Touring the City Runner Style

  1. OMG please let me know the next time you are freaking OUTSIDE MY DOOR.
    I have been wanting to do this, especially abroad–it has become a huge thing. Actually, we were considering doing this for Ramblen, but hadn’t quite fully developed the concept yet!

    • You know, that didn’t even dawn on me. It was a really fun time. I highly recommend giving it a go. Even in your own neighborhood or city, there is still so much to learn. All of their tour guides are top notch.

  2. That sounds like an awesome time! I have seen the philly running tour advertised several times but just haven’t taken the time to sign up yet. I would love to see more cities from the eyes of a running tour. Thanks for sharing!

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