The story
This past winter, my friend Sue and I were wandering around a huge flea market in Central Florida on my winter cycling getaway, looking at stuff I don’t need. I wasn’t shopping for anything in particular. Then I spotted him.
Hanging out in a booth was a plush Bob Ross with an oversized head, iconic afro, and radiating that classic “happy little trees” tranquility. I’ve been a fan since his TV days. With just three quick brushstrokes and a soothing word, the man could transform a blank canvas into an inviting mountain sanctuary.
There is an official Bob Ross YouTube channel. I never tire of watching it. Clearly, I’m not alone. His original paintings can sell for hundreds of thousands of dollars. By comparison, $10 for a plush Bob Ross is a steal.
I thought about it for roughly four seconds. Bob was coming home with me.
He returned to Ohio and sat on a dusty bookshelf. Little did he know he would become my bike tour companion, trailside celebrity, navigator, and co-pilot.
Wait, a 72-Year-Old Man and a Plush Toy?
Fair question. Over the years, I’ve noticed some long-distance cyclists ride with a mascot: a stuffed animal or quirky character that reflects a bit of their personality and story. Whenever I met one, I thought, “I need one of those.”
I mulled over the idea for far too long, picturing a realistic-looking bear rather than a teddy but something quirky enough to make people smile. A PBS celebrity never entered the picture.
Then I saw that Bob at the flea market. Calming presence? Check. Distinctive look? Check. A philosophy tailor-made for my view of touring? Happy little trees, absolutely. Happy little trails? Happy little hills? Now you’re asking too much.
Bob’s Big Debut
Bob made his touring debut in September on my Ohio to Erie Trail tour. I zip-tied him to the front handlebars, perched on the headlight, watching the world go by. Just like that, I had a Tom on the Trails mascot.
He was an instant hit. People yelled, “Hey, there’s Bob Ross!” as I rolled past. Others waved, grinned, or stopped for a closer look. Apparently, a plush TV artist strapped to an e-bike isn’t something you see every day.
It made me laugh and reminded me how a little whimsy can turn an ordinary tour into a memorable one. When I prepared for the Great Allegheny Passage, Bob’s place on the handlebars was assured, but first, he needed an upgrade.
Safety First, Even for Artists
My friends on the Ohio to Erie tour spotted an obvious problem: Bob had no helmet. In his defense, safety is easy to overlook when you’re a plush television personality. If he was going to log thousands of happy little miles, he needed protection.
Bob and I turned to Amazon, where a quick search led me to small dog helmets. I found one that fit his oversized head and promised to keep him secure on the trail.
A little creative engineering secured the fit. The helmet even came with sunglasses. Bob instantly went from quirky mascot to cool touring dude. His Afro spilled gloriously from beneath my stylish engineering triumph.
The helmet and cool shades made me smile. It was ridiculous in exactly the right way. That is the point.
Riding Solo, Sort Of
Solo touring on the GAP fits my style perfectly. It allows me to move at a leisurely pace, appreciate the little things, and spend time in my own head, whether I'm mapping out the next stop, dreaming up future trips, or preparing myself for the next climb.
With Bob up front, those inner conversations got a face. “Okay, Bob, water break.” “Bob, this is a perfect photo-op.” And when time for a mascot check-in: “Well, Bob, how do you think things are going?”
Yes, I talk to a plush toy. No, he doesn’t answer. Given his extensive and enduring TV career, he’s got plenty of practice talking to an invisible, unresponsive audience. Honestly, I’d be having these conversations in my head anyway. Bob gives them a face.
Plus, he’s a terrific listener. He never interrupts, never complains, “ Are we there yet?” Every bike tourist should be so lucky.
The Best Icebreaker Worth the Price
Meeting people is one of my favorite parts of touring. Bob is a natural icebreaker. A plush Bob Ross on the handlebars invites conversation. People stop, point, give a thumb-up, and recognize him even beneath the helmet and sunglasses.
I’m always surprised by how many people do. Some ask where I found him, and soon we’re talking about where I’m from, where I’m headed, trading life stories, lunch recommendations, and sharing the day’s news.
I seldom have to think of an opening line. Bob handles the introductions. He’s the best PR rep I’ve ever had, and he doesn’t even ask for a paycheck.
For a solo rider, those few-minute conversations matter. They turn a day of pedaling into something shared. If it takes a plush artist in sunglasses to make that happen. I’m all in for that.
Permission to Be a Little Silly
I love having Bob along. Somewhere as we age, we learn what grown-ups are supposed to do: be responsible, sensible, productive, and concerned about what other people think.
At 72, I’m less interested in all that. Why can’t a grown man put a tiny helmet on a plush toy and strap it to his handlebar? Who decided that a certain age means giving up things that make us happy? I don’t remember signing that agreement.
I spent years meeting obligations and others’ expectations. Those had their place and time. Retirement taught me that doing something completely unnecessary that makes me grin deserves a place in my life. Bob reminds me of that as he guides the way.
If someone thinks an old, bearded man riding with a plush Bob Ross is odd, they’re entitled to their opinion. I’m entitled to my ride. Besides, Bob looks remarkably good for 84. His perfectly coiffed Afro has survived miles of wind, rain, and questionable aerodynamic choices.
Here’s to Happy Little Adventures
Bob handled the GAP like a champ. Neither rain nor heat nor gloom of day could stay this plush painter from his appointed position on the handlebars.
His Afro held its shape, his sunglasses stayed put, and his helmet did its job. His only mishaps were occasionally needing to be returned to an upright position. Yeah, he occasionally dozed off.
I hope Bob joins me on many more tours, taking in the experience and not offering unsolicited advice when I’m lost, questioning my choices, or tackling a big hill.
“Hang on, Bob. We’ll get through this.” More often, it’s, “Bob, I think we’ve earned a break. Don’t you?”
Here’s my challenge: what would your mascot be? A bear? A dog? A favorite celebrity? Maybe something sitting on a shelf or tucked away in a drawer. It doesn’t have to make sense or be practical. You don’t owe anyone an explanation.
Pick something that makes you smile, zip tie it to your handlebar, and see who smiles or strikes up a conversation.
I’ll keep pedaling with Bob riding shotgun. After all, every trail could use a few happy little adventures.
What About You?
Do you have a bike mascot, or what would you bring along for the ride? Tell Bob and me in the comments. We would love to hear about it!
Happy Trails!
Tom on the Trails
