A Run Through Boston to Find Winnie the Pooh

by angierunsboston

As always, thank you to my heroes of the day! You could still be one for the next 25 days! My goal is to raise $500 in the next 25 days 🙂

Running can be as spontaneous or as stick-to-the-plan as you or your running buddies choose to make it.

A couple weekends ago, my friend (and life-photographer) Jeanie set out to run to Chinatown because she had heard of an event called the Oak Street Fair that would be going on.

“Free stuff!” she had exclaimed to me.

And that was all that I needed to hear.

Here’s something about Boston that I would tell newcomers. Look at a subway map of the city and you’ll think everything is incredibly far away. Run from one stop to another and you’ll realize how close everything is.

Taking the subway from Harvard to Chinatown means a 20 to 30 minute trip. Running from Harvard to Chinatown means about a 30-minute jog. See what I mean?

So, on that Saturday morning, Jeanie and I set out to find this Oak Street Fair. The plan was to run to Chinatown and soak up the childhood feeling of a fair – from photo booths to cotton candy to, of course, free stuff.  Then the spontaneity hit. After learning that Jeanie had never been inside the Boston Public Library (which is one of my Top 5 favorite places in Boston), I decided we were going to have to take a little detour to see what Jeanie later deemed a “mini-Versailles in Boston”.


The BPL courtyard is one of my favorite places…so of course we had to take a detour on our run and go there.

There are so many reasons I love the BPL. It’s pretty. It’s the first public library that let patrons borrow books and take them home. It has a courtyard that transports you out of the city and into a Renaissance palace in Rome (which the architect was reportedly inspired by). So, of course, I forced Jeanie to spend five minutes in the courtyard before we continued on our way to the fair.

After getting slightly lost (or as I like to call it, “extending the adventure”), we made our way to the fair only to be greeted by none other than Winnie the Pooh at the entrance. He even convinced us to do a kick line together!


Running sometimes leads to kick-lines with Winnie the Pooh. More incentive to run?

Despite being a little sweaty from our run, we became fast friends with Pooh and then made our way inside, where we planted flowers, made a nostalgic layered sand jar (bet you haven’t done that since 3rd grade), and cheesed it up for the photo booth.

All in all, I would call that a successful run. Sometimes, a run can be spontaneous while sticking to the plan all at the same time.

As always, let’s hope I can keep that spontaneity/plan-following up for a whole 26.2 miles!