The Trip I Never Expected

The Trip I Never Expected

“So you want a Pepper Ride?”

What could go wrong? It was a beautiful day in Negril, Jamaica. A bit warm and humid, perhaps, but we were about to go play bikes in a foreign country. This was one of my favorite definitions for fun. The night before at dinner, I’d learned a few unexpected facts about our tour, stuff that hadn’t been apparent for the tour’s web site. The first was that our guides didn’t just occasionally ride bikes, like when the tourists arrived. These guys were racers and our lead guide, a guy with the nickname Fowly, was a multiple Jamaican Master’s National Champion. His kid, who was called Chicken, was going to be along, a guide in training. Chicken is the current Jamaican National Champion. Normally, these guys did a ride on Wednesdays and Fridays called the Pepper Ride. They’d kill it out of Montego Bay, hit Lucea, turn around and then light it up for the headwind back into Mo Bay, as the locals call it.

A group ride with the local killers in a foreign land? Oh hell yes. I dream about this stuff and rarely have I ever had the chance.

IMG_7937It was rare that we weren’t within view of the water. 

So, yes, I wanted a Pepper Ride. Or so I thought.

When we rolled out of our resort, the pace was easy as first-grade math, maybe 14 mph. It was an easy spin in the morning air with ready views of the turquoise water to our left. Gradually, the pace rose: 14.5, then a mile or two later 15. After 20 minutes we were doing 19 and the group was still holding together. While all of the clients were riders on their own bikes, there were varying levels of devotion and fitness. Eventually the group split into two groups with the front group accelerating just a hair more while the rear group eased off by a mile per hour or two.

IMG_3854Jerk shacks were as plentiful as they were low-tech.

One of the other details I really hadn’t been clear on was the situation with the two motorcycle cops. At every other cycling event in which I’ve participated, the police escort is firecracker brief, just long enough for them to claim they did it, as if they were the booster engine that got us up to some imaginary pace to increase our safety. So I expected our two escorts to get us out of town and disappear. Every time one of them zoomed ahead of my group I figured, “Okay, that’s it; wave goodbye.”

They never left us. They spent the entire day controlling both the oncoming traffic and the cars that approached from behind. One would ride slightly ahead of us and motion the oncoming cars onto the shoulder as the vehicles behind would be waved ahead in the oncoming traffic lane by the officer behind us. We simply occupied the lane we were in. No shoulder riding for us. No matter what speed we rode, the motos accommodated it. The traffic was never-ending, but also never dangerous (for us). It appeared as near-mayhem most of the time, but everyone yielded right-of-way without significant complaint. I catalogued two yells and two locked up brakes (oncoming traffic), but all day, every day, these guys were with us. Let me clarify: Driving in Jamaica is chaotic when it’s going well, and while I didn’t see the crazed fatalism I’ve observed in the drivers in other third-world countries, between the debris on the shoulder and the sloppy four-wheeled ballet that took place on the roads, I’d never tour in Jamaica by bike, on my own. But this? This was genius.

So when this kid too skinny to throw a draft went to the front, I figured I was about to have fun. As the pace neared 30 mph, the group shrank like some god was hitting the delete key. I was relatively certain I’d be able to hang on until we rounded a bend and the ocean breeze became a firing squad and the quark at the front of the group stood up to stretch his legs. As they sped away like a peloton of dragsters under a green light, I noticed that I was on fire both in my muscles and on my skin.

IMG_7983It was sometimes difficult to tell the pets from the evening meal.

What the hell had I agreed to? Two more days of this and I’d need an ambulance to get to the airport.

I arrived in Montego Bay not really knowing what to expect. On other tours I’ve done, the game plan was always pretty obvious; you go to the Alps to climb the Col du Galibier and l’Alpe d’Huez, the Pyrenees for the Col du Tourmalet. Tuscan tours are meant to lead riders past one idyllic vineyard after another. But what was the point of a bike tour in Jamaica? I wasn’t really sure.

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  1. Wayne Miller

    Great story. There are guys who regularly do rides from Kingston to Negril.

    You should check that out.

  2. Full Monte


    This piece is already in the running for Why We Ride II.

    On your return trip, I’d love to hear more Ms Hilton.

    BTW, I may have a move coming up in the near future. Which means, time to edit cycling gear. I don’t suppose there are many L sized kids in Jamaica, but I feel compelled to ask. If so, what’s a good address?

  3. Peter


    Thanks not only for writing this ride up so clearly, but also for your insight into the people and places we visited on this tour and your on-bike, on-a-roll photography.
    Myself, the challenge of the tour itself has been a fitness boost which I’ve felt right after signing up, while on the tour, and following. That’s one of the reasons I plan to return in November.
    One technical bicycle question: Do you think it is a good idea to install a mountain bike cassette for the Cat 4 climb of this ride? I’m thinking a road cassette suits this ride the best due to segments like MoBay to Ochi, where finding just the right gear within a standard range is the way to deal with the headwinds.
    thanks again,

    1. Author

      Everyone: Thanks much for the kind words.

      Full Monte: There are master riders who could definitely use your cast-offs. After all, masters are just big kids. I can give you details if you’ll email me at the [email protected] address.

      Peter: I’d like to think most riders could get through day two’s steepest stuff without a mountain bike cassette, but the moment you make a broad statement like that, you run across someone who simply needs more gear. I *suspect* that a 34×27 will be enough for even moderately fit riders.

  4. Pat O'Brien

    That was a sweet read. Thanks.
    The guy in the picture has legs like Marty Nothstein in his prime. Bet when the sprint started no one was holding his wheel.

  5. Don Seven

    I have been out of the Red Kite Prayer loop for a while, return to find the perfect gem that is the Red Kite Prayer! Excellent job describing the contrasting experiences of your tour.
    Having lived, traveled, and cycled throughout South America you captured the essence of many realities. Thank you.
    Be well.

  6. Storm

    How awesome it was to read about our ride in Jamaica, from your perspective. I am humbled that we as a people, touched you in such a special way. I am happy that you appreciate what we are trying to do with our ride. It’s more than showing cyclists our country,but also provides employment for Jamaican cyclists and brings them in contact with cyclists from other countries. That interaction is invaluable. Thank you for coming and thank you so much for your ongoing support to our cyclists since your return. You are an amazing communicator and honest to a fault. I respect that a lot. That you would rate this as your best trip ever…well its the best compliment any tour operator could ask for! Thank you. Thank you. Thank you! And as we say in Jamaica…One love! Storm

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