The Top Questions People Ask Me When I’m on a Bike Tour
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When you’re hauling a trailer behind your bicycle through small towns and stopping at gas stations or convenience stores, people are going to have questions. A lot of questions.
And honestly? I enjoy it. Striking up a conversation with a curious stranger at a truck stop or a roadside store has led to some of the best moments of my tours. So today I thought I’d share the top things people ask me when they meet me on the road — and how I usually answer.
1. “Where are you going?”
This is always the first question. People see the bags, the gear, and the trailer and know I’m not just headed to the next neighborhood.
2. “Where are you from?”
Right after that, they want to know where I started. And when I say I’m from Lubbock, Texas, they usually raise an eyebrow — especially if I’m halfway across the country by then. A lot of them know Lubbock because of Texas tech and lately because of Patrick Mahomes.
3. “How long will it take you to get there?”
People want to wrap their head around the timeline. I tell them how many days or weeks I’ve planned, though in truth, touring rarely goes exactly according to schedule.
4. “How far do you ride each day?”
This is one of the most common follow-up questions. When I tell them I might ride 60 miles one day and over 100 another, they look at me like I’ve just claimed to ride with wings.
5. “Are you crazy?”
And there it is — always next in line.
If I’m having a tough day, I’ll laugh and say, “Maybe I am — today sure feels like it.”
But if I’m feeling good, I usually grin and say, “No, I think everyone else is crazy for not doing this.”
6. “Why are you doing this?”
Some assume I must be raising money or riding for a cause — and sometimes I have. But more often, I do it simply because I love it. I love the freedom, the rhythm, the quiet roads, and the deep sense of connection I feel with the land, my body, and even strangers I meet along the way.
7. “Does that trailer make it harder to ride?”
They’re usually eyeing the gear I’m pulling when they ask this one. I tell them that on the flats, I hardly feel it back there. But start me up a hill and it’s like dragging an anchor.
8. “Do you sleep in a tent or stay in hotels?”
The answer is both. It depends on the day, the route, the weather, and what I’ve planned ahead. Some nights I pitch a tent in a quiet park or campground. Other nights, I treat myself to a shower and a bed.
9. “What do you do if it rains or gets really windy?”
Women ask me this more often than men — out of concern, I think. I tell them I’ll ride in the rain as long as there’s no lightning nearby. I’ve got good gear to stay dry. And as for wind? I’m from Lubbock — the third windiest city in America. Wind and I are old friends.
10. “Has anyone ever messed with you or been mean?”
This question usually comes from men, often with a protective tone. I tell them the truth:
The people of America have been fantastic to me. I’ve ridden thousands of miles across this country and the kindness I’ve been shown far outweighs any fear or negativity.
11. “How many miles will it be total?”
This one comes up toward the end of the conversation when people start to really grasp the scale. Sometimes I know the answer. Sometimes, I just smile and say, “A lot more than most people would want to do.”
Final Thoughts
I never get tired of answering these questions. They remind me that bicycle touring is still a bit of a mystery to most people — and that curiosity is a beautiful thing.
So if you’ve ever met someone on the road pulling a trailer behind their bike and had these same questions, don’t be shy. Ask. You never know what kind of stories that rider has to tell.
Let me know if I missed a question — or if you’ve ever toured and heard a few I didn’t mention. I’d love to compare notes.
More Stories from the Road from the Old Guy
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