Daniel Varghese is a writer and editor and runs the Substack newsletter Leg Day, chronicling his pursuit of the joy of cycling as an urban rider, and his journey into the sport. This is the first of several beginner-focused pieces he’ll write for Escape Collective.
Soon after I started cycling in New York last year, I did a quick survey of all the group rides I could find. There was a pretty impressive range on hand, but none immediately appealed to me. I didn’t know how to ride in a paceline or ride clipless, a prerequisite to join some of the speedier cycling teams I found. I was wary of riding in a rowdy crowd, which rules out some of the most prominent social rides that draw over a hundred cyclists (and reportedly some motorcycles). And I wasn’t confident I could get myself home if I joined the group that rides to a different brewery every week, especially since they often end the rides well after the sun has set.
I decided to start my own. For most of last fall and into this spring, I managed to convince a few of my friends we should ride from our neighborhood into different parts of the city, usually with a stop for cortados and pastries. The rides were a salve, especially in the winter. In previous years, bad weather would have kept me in bed. But it was easy to wake up when I knew I was going to get to spend the next few hours riding with friends.
I’ve since gained a lot more confidence on the bike and had the opportunity to join a number of more public group rides. I’ve enjoyed some of the more fitness-oriented ones I have tried, but have much more fondness for more causal rides through the city with oddball destinations. If you’re not so lucky to live in a city like New York, with all this choice, I’d encourage you to try starting your own as well. To aid, I’ve gathered the tips I’ve gained from experience, as well as by speaking with a number of ride leaders from across the U.S. (Don’t worry Aussies, there’s nothing hemisphere-specific about the advice below.)
Start with your ride goal
All bike rides have a primary purpose, be it function, fun, or (god forbid) fitness. Identifying this aim should be the first step in planning any group ride. The actual goal can be whatever you want. Ralph Phillips, owner of Fair Wheel Bikes in Tucson, Arizona, co-founded the now weekly 71-mile Shootout Ride in the 70s because he and a friend wanted a regular training day that simulated race conditions. Lana Pochiro, founding member of Bad Pony Racing, also started running an weekly open-invite fast-paced fitness ride in Brooklyn’s Prospect Park to create a space for people that rode fixies. (Also one where they weren’t the only non-man present.)
Even if your ride is weekly, it doesn’t always have to have the same aim or route. Earlier this year, KK Glore took the other members of Brooklyn’s Non-Binary Bike Club on a “Fish Tour” of “places in New York City where you can just gaze at fish for free,” they said. “It felt like I was sharing some kind of secret knowledge with the group.”
A clear goal can and should inform every further aspect of your ride plan. You’ll be able to tell people how fast you plan to go and how hard the ride will be. You’ll be able to know whether to design your route for the shortest distance or for comfort and safety. You’ll know how many people you want to try and invite to join you. And you know what to prioritize if something goes wrong.
Just make sure your ride goal actually makes sense for your group. Glore led a ride a few years ago for a group of relatively new cyclists over what they thought was a simple city route with a planned boba stop. Unfortunately, everything that could go wrong, went wrong. “We had an aggro driver speed through the group. We had someone fall and get banged up and scared.” Because so many of the riders were beginners, and the fall happened on a particularly busy stretch of road, Glore struggled to get everyone to safety and ended up having to split up the group.
Set expectations early
Once you’ve thought through the reason for your ride, think about how to plainly communicate it to any prospective rider. There are a number of ways to communicate these expectations. Mark Alford of Venice, California, the US west coast marketing manager of Rapha, says the company posts details about its rides on its website, app, and Strava Group. You can find all the information you need about the weekly Arizona Shootout ride on the Fair Wheel Bikes website. I have found success posting flyers for rides I’ve planned on Instagram and in my newsletter.
At minimum, you should make sure to provide a short explanation of the ride goal, the total distance you’re planning to ride, the start point, the end point, the route you’re going to take, the speed at which you’ll do it, and whether the ride will “drop” anyone who can’t keep up. Neglecting to do so, said Alford, could create “unsafe conditions.”
Making sure I’ve clarified what people are going to experience before a ride starts has also helped allay my very American anxiety that one small mistake will get me sued. In case you’re also worried about litigious participants, know that you most likely can’t be held liable for something that goes wrong on a casual group ride. Obviously, there are exceptions, said a partner I spoke with at Lucarelli & Castaldi LLP, a New York City firm that specializes in cycling crashes, but you really only open yourself up to a lawsuit if you’re planning a large event where people are expecting road closures, ambulance support, and/or police escorts.
Plan your route
Many regular group rides have the same start and end point each meeting, especially if their ones like the Shootout that are intended to be ridden quickly. “You’ve got to find a route that you feel is safe, but also one without a lot of traffic,” said Phillips. The Shooutout ride is additionally planned so that there are very few stop signs and lights after its neutral start.
Making the routes available is of particular importance if your group is taking a route they haven’t before. The Non-Binary bike club always meets at Ride Brooklyn, a bike shop in the Park Slope neighborhood of New York, but rarely repeats a destination or route. Glore usually makes their routes in RideWithGPS, which they include in the announcement post for every ride. The app also allows them to share the route with any rider that wants it, which they say helps both so that everyone is aligned on their path and in case anyone wants to join up with the crew midway through the ride. Strava’s Global Heatmaps can also help you identify the most frequently used segments in any given area. But I wouldn’t recommend you use that app’s route creation tool—I’ve been sent the wrong direction down too many narrow one-way city streets.
Know your audience
Make sure that the way in which you’re discussing elements of your ride makes sense for the people you’re planning to ride with. For example, road cyclists commonly list the expected pace of the ride in miles or kilometers per hour. These metrics don’t necessarily mean anything to the average, more casual cyclist, especially if they ride in a city where they often have to stop as a cyclist. “I’m allergic to pace numbers,” said KK Glore. “Like, what the fuck is 13 miles per hour. I don’t know, don’t ask me.”
Recently, I planned a group ride to check out three new coffee shops I hadn’t yet visited. I wanted the ride to feel accessible to anyone, no matter their equipment or experience level. So instead of just dropping “10 mph” on the flyer and calling it a day, I wrote that we would be doing the ride at “Jalopy Pace.” In the description for the ride, I explained I wanted the group to move at a speed that could be maintained on a bike that was one stiff breeze away from falling apart.
Sure, this is a bit silly, but it had the intended effect. Even though only a few folks could actually make the ride—it happened on the first truly cold Friday morning of the fall, when the forecast said it was going to rain—one person came out with their 80s-era single speed bike. She had lived in New York for over a year, but this was the first group ride she had ever attended. Given how much fun we had, I am hopeful it won’t be her last.
Embrace the icebreaker
Before anyone starts pedaling, the ride organizer should take a moment to introduce themselves and identify the group’s ride leader, so everyone knows who to follow. If the ride is “No drop,” designate someone as a “sweep” who can sit towards the back of the group and make sure no one gets separated on a climb or because of traffic.
If the group is small enough and the ride is intended to be social, consider curating a “corny” environment, Pochiro says. They make everyone say their names and sometimes pose a question for all the participants to answer. “I’m a big fan of being cheesy. You don’t need to be cool. You’ll have a better time if you’re not cool,” they said.
The weather had been so bad in the days leading up to the aforementioned coffee ride that icebreakers felt totally unnecessary. I had already individually spoken to the two other people who were in attendance to assure them that the ride would happen rain or shine. Ultimately, the conditions we rode in were unideal—intermittent sprinkles, powerful winds, a just-above freezing temperature. The three of us quickly bonded over the worst conditions we had ever ridden in, swapped cold weather survival techniques, and erupted with glee when the sun poked its head out from behind a cloud for one blissful minute.
By the time I made it back home, only about three hours after I had begrudgingly rolled myself out of bed, I was bouncing off the walls. Sure, this might have been the four cups of coffee I had consumed that morning, but it felt like it had more to do with the time spent getting to make new friends. The fact that I had technically worked out barely registered.
Next time I’m in a biking funk, I know how I’m going to motivate myself to get back in the saddle. Who wants to go get some coffee?
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