The Top Questions People Ask Me When I’m on a Bike Tour
Last Updated: September 5, 2025
11 Common Questions People Ask Bicycle Tourers (And My Answers)
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| That question is the single most asked question I get asked when I meet people while I am touring |
That’s touring life in a nutshell. Hauling a trailer into small towns, you’re going to attract questions. Honestly? I welcome it. Some of my favorite touring memories come from these conversations at truck stops, diners, and roadside stores. Here are the most common questions—and my honest answers.
1. “Where are you going?”
Usually the opener. People see the bags and know I’m not out for a neighborhood loop.
2. “Where are you from?”
When I say Lubbock, Texas, I usually get raised eyebrows—sometimes a Patrick Mahomes reference.
3. “How long will it take you?”
I share my rough timeline, but touring rarely runs on schedule. That’s part of the adventure.
4. “How far do you ride each day?”
60 miles one day, 100 the next. That always blows their mind.
5. “Are you crazy?”
I laugh and say: “Maybe today.” Or if spirits are high: “No, everyone else is crazy for not doing this.”
6. “Why are you doing this?”
Sometimes for a cause, but mostly for freedom, rhythm, and connection with the road.
7. “Does the trailer make it harder?”
On flats, no problem. On hills? Feels like dragging an anchor.
8. “Tent or hotels?”
Both. Weather and budget decide that for me.
9. “What if it rains or gets windy?”
I ride unless there’s lightning. And I’m from Lubbock—the wind capital. Wind and I are old friends.
10. “Do people ever mess with you?”
Almost never. The kindness I’ve experienced on the road outweighs any negativity.
11. “How many miles total?”
Sometimes I know, sometimes I just smile: “More than most people would want to ride.”
Final Thoughts
These questions never get old. They remind me that touring is still a mystery to most folks—and curiosity is a gift. So if you see a rider pulling a trailer, don’t be shy. Ask. You might walk away with a story too.
🚴 Gear That Makes Touring Easier
- RENPHO Solar Scale — Track your fitness progress while on or off tour. I was at a weight plateau for months before buying this scale. The information it gave me provided the insight and the motivation to bust through my plateau and lose an additional 17 pounds to get me to my perfect cycling weight. The cost was nothing compared to the benefits it gives me.
- Giro Fixture MIPS II Helmet — This is non-negotiable. You must wear a helmet and you better get one with MIPS technology. I wear the Giro Fixture MIPS II Helmet. If your head ever hits the ground you will be happy you have the technology. Here is the technical stuff about MIPS
- Padded Bib Shorts — Comfort that makes long days in the saddle survivable. Here is a collection of great padded shorts. The Pearl Izumi shorts are highly rated. I wear the Przewalski shorts but some people find the padded insert not as good as Pearl Izumi or Le Col. I have rode long enough that my but has toughened up and I prefer lighter padding. That is why I am giving you a choice here.
More Stories from the Road
- From Triumph to Breakdown: My San Diego Cycling Disaster
- Caught in the Storm: The Night I Thought I Might Die in Bowie, Texas
- The Rides I’ll Never Forget: Cycling Memories That Last
FAQs About Bicycle Touring Conversations
Do people really ask “Are you crazy?”
Yes—almost every trip. It’s the question people can’t resist.
How do you keep the conversations positive?
Smile, keep it light, and share the joy. People usually walk away fascinated, not judgmental.
Do these conversations slow you down?
A little. But they’re worth it—the stories stay with me longer than the lost minutes.
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