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Lucy Flanagan

Lucy Flanagan of New Trier, was a hiker who worked at an indoor cycling studio but didn’t really ride outside before deciding to do her first ever bike tour through Overland: a coast-to-coast trip going 3,248 miles from Savannah, Georgia to LA. Now she loves biking and is planning to ride through the Canadian Rockies this summer!


What did you do to prepare?

Most of my physical preparation was from my indoor classes, but I also had to get used to my bike and the rules of the road. Hills were hard to train for since Illinois is so flat, and it took me a bit to figure out how to load up my bike, but since I genuinely wanted to be there, I got used to it quickly.  

What kind of gear did you need? 

I got a Trek 520 from Wheel & Sprocket. I used two panniers, a frame bag, a rear rack and bungee cords to carry my gear. I had a sleeping pad, sleeping bag, multi-tool, tire levers, spare tire and tubes. I wore cycling shoes, shorts with a chamois and my bright WaveCel helmet. I found a hydration pack easier than grabbing my bike bottles, especially while climbing. 

What was a challenge you weren’t expecting?

It was more of a mental challenge than a physical one. We went about ninety miles a day, 15mph, carrying fifty pounds of gear, so you’d think physical fitness would be more important, but you also have to really want to be there. Waking up every day at 4AM and going through the same conditions was really mentally tough. We also didn’t have our phones with us, which I liked, but being away from everything for six weeks was definitely an adjustment.

What are some fun memories?

Our last day in the Oklahoma panhandle started with terrible headwinds, we climbed all day in the middle of nowhere looking at nothing, but the last 20 miles was a descent that ended in New Mexico in the middle of the Rockies. Seeing that change right before my eyes was incredible. And I made some of the best friends doing this; we became close in ways I cannot describe. 

What did you learn?

I was dreading the south because of the heat, but the support we got was incredible. We stayed in a lot of churches that would often have dinner prepared for us, and in Mississippi, the local fire department gave us a firetruck escort for the last five miles into town. They had a buffet and mattresses, and they drove us to their pools; it was amazing. I’ll never forget that. The towns we visited were so far from my own life in the North Shore; it really opened my mind. 

How do you use your bike now?

I wasn’t a cyclist going into the trip, and I wouldn’t really call myself one now. I’m just someone who has a really strong connection to my bike, so I ride it when I can. I prefer using my bike to get around: you can whiz past traffic, it’s more environmentally friendly, and you’re combining your commute and cardio, so why wouldn’t I? 

What would you say to someone who looks at bike touring and thinks “I could never do that?

If you’re not a bike whiz, it’s simpler than you think. You should learn how to change a flat and figure out how you’re carrying your gear, and it’s just riding your bike after that. In my opinion, if you want to, you can always do it.