The Best Running Tour of Boston

Updated July 21, 2020.

I don’t know about you, but running is one of my most favorite travel activities. On my recent trip to Boston, I went on my first ever running tour, and it was a fabulous way to see the sights. I chose a private tour, but you can do a group tour as well. I went with the company Run Boston, and Brendan was my guide. Here’s a little insight on my tour and what to expect if you want to do a running tour of Boston as well!

Know Before You Go

Okay, if you plan on doing a running tour, odds are you already know how to run! But there are a few things to be aware of in advance.

The Process

Scheduling a tour with Run Boston was very quick and easy. You can even tell them what you want to see and what you’d prefer to skip. They will be in touch with you within 24 hours, and they will match you up with a great guide! Brendan is a nurse by day and a native Bostonian, making him a fantastic running buddy!

The Weather

You probably already know Boston is exceptionally cold and snowy in the winter. But did you know it can be hot and muggy in the summer? Check the forecast and pack appropriate running gear! Also, remember to hydrate before and after, and bring water with you if necessary. For my complete guide to running on travel, check out Running Around the World!

I never knew Boston could be so balmy in summer!
More here: What to Know Before You Visit Boston

My Route

Your guide will customize your route to your requests and specific running needs. They know the territory, so they know the best places to go and the best ways to get there! Your route will likely differ from mine, but here is an example:

My Boston Running Tour Route via MapMyRun!


My whole tour was fun and interesting and informative, but in case you’re interested, here are the highlights!

My Hotel

We started at my hotel, the Omni Parker House. Not only is it perfectly situated on the Freedom Trail, it is also the birthplace of Parker House Rolls and the Boston Cream Pie! But Brendan was able to tell me a few more things about it that are a bit lesser-known. For instance, Charles Dickens lived (and wrote!) here for 5 months in the 19th century. The Kennedys have connections to this hotel (it’s where JFK proposed to Jackie!). And it is the oldest hotel in Boston!

Omni Parker House Hotel

Boston 0 Mile Marker

I surely would have missed this if I hadn’t had someone pointing it out to me! All measurements from Boston are measured from this point in the historic center of Boston.

Boston Zero Mile Marker
Don’t miss a thing! 1 Day in Historic Boston

The Tiny House

I have a soft spot in my heart for tiny houses! I love how this one is just peeking up over the Copp’s Hill Burial Ground. Kind of spooky, kind of cute!


MIT and the Charles River Running Trail

Can you believe I didn’t get a photo of MIT?! Total blogger fail. I asked specifically to run by MIT because my sweet husband got his Master’s there long before I knew him! I got to run along the Charles River Trail, where he would also run while he was living there!

I didn’t get a photo of MIT, but I did get this picture of the sun hitting the flowers just right!
More here: 10 Things to Do in Boston


What is a “Smoot,” you ask? It’s a unit of measurement used to measure the bridge to MIT! Smoot was a student at MIT who wanted to join a fraternity, so his potential frat brothers tasked him with measuring the bridge according to his height. To this day the bridge is measured in Smoots!

The 50-Smoot Mark

Boston Marathon Finish Line

I am not made for marathons, but I sure love to run! My sweet husband has run four marathons, and in fact we first met each other at his fourth marathon! Brendan made sure our route included the last two turns of the official Boston Marathon (“left on Hereford, right on Boylston!”), and he kindly snapped this pic at just the right moment, at the finish line of the oldest marathon in the country:

The Finish Line!

Are you ready to run Boston? Tell me below! And while you’re at it, check out my United States Page for everything you need and more!

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3 responses to “The Best Running Tour of Boston”

  1. […] Unless you are running the race, plan your visit for a different date! The race is historic and a tremendous money maker for the city, but that comes with large crowds and closed streets. General tourism will be better a week or so before or a week or so after the marathon. Want to run in Boston without the crowds? Take a running tour! […]

  2. […] a little more time? Take a tour! My running tour with Run Boston was fantastic, but there are also walking tours, ghost tours, and more to choose from! Just do a […]

  3. […] Keep reading: Nantucket by Land and By Sea,Biking Block Island, and Running Boston […]

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