How-To: Leading a Group Ride

Our posts about group rides nearly always draw comments like “I wish we had one of these in my city” or “I’ve been wanting to organize something like this, but . . . [insert excuse here].” I used to be one of those commenters, until the Garden Party Ride here in Nashville showed me that yes, Virginia, we could host our own cycling event.

The Nashville Garden Party Crew

The Nashville Garden Party Crew

You can, too! And you should. Group rides like these are a lot of fun, and in my opinion they’re even better than Critical Mass for raising community awareness of city cycling. Here’s how to get started.

  1. Pick a theme and a date. Tweed Rides are always popular this time of year, but you can try any theme that might go over well in your community (SlowBikeMiami is batting around the idea of a Miami Vice Ride–talk about a fun theme). As for times, I like early evening in case some people are uncomfortable with nighttime riding or don’t have lights. In winter, of course, riding in the dark is unavoidable.
  2. Dottie dressed for the 2009 Tweed Ride in Chicago

    Dottie dressed for the 2009 Tweed Ride in Chicago

  3. Where are we going? Pick spots that fit with your theme. Pick spots that will have room for your group, and if possible, call ahead. Decide how long you want to stay at each place and let your group know when it’s “last call.” It’s best to put at least a mile between stops; otherwise you won’t feel like you’ve had a real ride. This is especially important if your ride is for drinks only, since people will need a chance to burn off those cocktails. And if you think you’ll have people driving to the starting point, ending your ride where it began is a necessity.
  4. How do we get there? Keep the skill level of your riders in mind. If you’re going to have a lot of newbies, try to stick to calm streets or bike lanes (this is also a good idea if it’s your first time leading a ride). A normal distance for a fun ride is 8-12 miles. Depending on the size of the group, you may want to print out a map for your participants. If you end up selecting a route you don’t ride regularly, TEST IT OUT before the big day. The last thing you want is to get lost or end up on a road that is under construction, etc.
  5. Dottie and Elisa of Bike Skirt on the last Chicago Cocktail Ride

    Dottie and Elisa of Bike Skirt on the last Chicago Cocktail Ride

  6. Fearless leader wanted. Decide who will lead the ride. You’ll also need someone to sweep the back and holler if people get too far behind or stuck at a light. Ideally, you’ll have a leader, a sweep and someone in the middle (this depends on the number of riders, of course). If any part of your ride will take place after dark, the leader and sweep must have lights.
  7. Advertise. If you have a blog, that may be all you need, but a Facebook event page or an evite can work just as well. Or design a flyer and put it up at your LBS. Consider mentioning whether the ride will be rain or shine, or rescheduled in case of rain. Of course, tell your friends and family.
  8. Me on the June Chicago Cocktail ride we co-organized with John Greenfield

    Me on the June Chicago Cocktail ride we co-organized with John Greenfield--working with an experienced organizer is a great way to build confidence.

  9. Have fun! I guarantee you’ll be wondering why you waited so long to host your own ride.

Questions? Leave them in the comments. And if you organize a cycling event in your city, let us know!

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36 thoughts on “How-To: Leading a Group Ride

  1. Elisa M says:

    Dottie and I came up with the next ride idea: PROM! wear your old Prom dress (or hit up the thrift stores) and the ride ends up at Red Lobster or Olive Garden. Such fun!!
    Organizing a group ride can be daunting, but if done right, a ton of fun. You ladies know how to do it well.

  2. Trisha says:

    Dude. That is brilliant! I should have mentioned that having your experienced self on our Nashville ride was quite welcome, BTW. ;-)

  3. Ha, looks like we’ll have to do the Miami Vice Ride now at some point! :-)

    Funny, cause last night as we were having birthday sushi (sorry, I’m shameless about saying it was my birthday yesterday) we were talking about the idea of hosting a ride. My wife isn’t too keen on the Miami Vice theme (though I think it would be a hoot) but we were talking about 1920’s boomtown era: Miami Beach, Art Deco, Flappers and Big Band (and of course Gangsters). This was the first golden age of Miami, and is not too obscure. We’re batting the idea around. Your post just came in right on schedule to help me think about what I need to plan for.

    We’ll see how it goes.

  4. Rich says:


    So when are you going to put together a Tweed ride for Nashville. I’ve thought about trying to get a couple of co-workers up for one but haven’t thought about expanding it to greater Nashville.


  5. Ira says:

    Group rides are fantastic, and as you point out, easy. Our pub crawl series has become very popular and requires very little organization.

  6. Catherine says:

    Re: winter riding=dark riding.

    I have to admit, I’m fairly terrified of this prospect and think I may wind up abandoning my bike commute for a bike-to-the-Metro kind of “commute”. Any tips for overcoming fear of the dark (riding in the dark that is)? I’m thinking specifically of the trails–riding on the streets at night wouldn’t be that bad. But all-but-abandoned wooded trails even at only 6pm–it’ll be pitch black and a little bit Little Red Riding Hood-esque to me :(

    • dukiebiddle says:

      Are there any practical “all-road” routes that are bicycle safe from a Potomac crossing to Alexandria? Howzabout a commuting buddy?

      • Catherine says:

        None that I know of (or can find using Arlington and Alexandria’s bike maps). The trouble really is that the Pentagon grounds and Arlington Cemetery are pretty much between Alexandria (and South Arlington) and the river crossings.

        I have been kicking around the idea of a “bike pool”–people who agree to meet up at the Jefferson Memorial or somewhere before heading over the 14th Street Bridge to then ride the trail together (just realized that I’m assuming you’re local–if not, sorry for the random geography). I think that could be a good solution, but would also require me being much more strict about my commute times (which actually would be good for me in other areas of my life–but it’s just so darn hard to do!)

        • dukiebiddle says:

          I left the D.C. suburbs for Baltimore about 12 years ago. I’m not that sharp when it comes to the Virginia routes, but I’m vaguely familiar.

          If people can work out car pools, I can’t think of a good reason why a bike pool couldn’t be worked out, especially if organized by an area cycling organization, especially emails and texting and twitter, etc.

    • dukiebiddle says:

      You know, the more I think about the notion of a commuting buddy, the more I think that someone at WABA should try to set up some sort of a winter convoy program. Everyone heading to Old Town meet at the Monument @ 5:30, everyone heading up Rock Creek Park meet at the whereever @ 5:30 sort of a thing. It could work.

      • Catherine says:

        Ha, I was still writing my response when you wrote this. Yes, it could work with enough people so that there would be several departure times. Some people leave work at 5, our library (and much of the Hill) doesn’t close until 6 and the lawyer types….well, they don’t ever depart work so maybe they don’t count ;).

        I emailed WashCycle about this idea and he said he’d post on the blog to help out the effort if I wanted to organize something. WABA would be good, too, of course.

        And I change my Jefferson Memorial vote to the Washington Monument–better lit and still after 5 years of living here (about half of them working on the Hill) I haven’t gotten tired of looking at the Capitol Building lit up at night :). A much better place to wait for the convoy indeed.

        • superbk says:

          Sounds like we have some DC commuters here! What say we organize ourselves a fun ride? I know WABA does the Bike Prom, but we need something more than once a year.

  7. miss sarah says:

    Man, I was just pitching a November ride to my crew. Like, my regular CYCLING crew and all I got was a lukewarm response. Somebody was concerned their road bike would be bad if there was snow (okay, fine) and others were like, “I’m not sure if my girlfriend wants to ride when it’s cold out.”


    I’m going to do it anyway.

  8. critninja says:

    my girlfriend and i organized a handful of rides this summer in calgary including a “full moon in june”, an ice cream ride, a pedal potluck, and a pubcrawl – all of which drew out more people than the local critical mass ride.

    i agree 100% that these rides can do just as much for cycle awareness as a critical mass – but with fun as its main focus, not antagonizing motorists. my personal feeling is that the general (motoring) public looks at these fun rides much more favorably and we did not have one single problem during all these rides.

    if your town/city doesnt have a ride – START ONE YOURSELF!

    it only takes 2 people on bikes to make a statement.


  9. critninja says:

    sorry – one more post – as my blog link wasnt working. hopefully it is one this post.


  10. Our local Freakbike Militia sponsored a Summer of Love ride that was the best group ride I’ve ever been on.

    Their big ride of the year is Halloween. THAT one should be strange.

    I used to organize regular Full Moon rides on the Lake Okeechobee Scenic Trail.

    Including this one where I talk about the difficulty in herding cats:

  11. Christa says:

    This is very helpful, thank you!

    My friend and I are planning a Cycle Chic ride in November. Theme: Red Carpet Riders… so SoCal. :)

  12. This is great. I have been trying to plan a cycle tour to raise funds for my graduating exhibition. I know at least a few enthusiastic people that will spread the word and just need a few sponsors…

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