First, I researched. I looked at Amazon’s top-rated products and their user reviews. Then I consulted Bicycling magazine, Gear Junkie, Bike Radar, Outside, and the occasional bit by Lennard Zinn via Velonews. I also found some worthwhile discussions at Bike Forums. Then I spoke with four experts, Ramona Marks, Scott Karoly, Cari Z, and Alison Tetrick, riders from all across the spectrum, who tour, repair, and race.
As you mentioned, it is surprising how often you can get multiple flat tires on while riding, particularly on longer sprints. The tip about bringing a patch kit in your bike repair kit can be incredibly helpful if you’ve already had one flat tire. I agree that all you listed seems like an awful lot to carry, but it’s always better to be safe than sorry, isn’t it?
For the budding mechanic:  A good pocket sized repair guide.   One good option is the “Pocket Guide to Emergency Bicycle Repair”  by Ron Cordes and Eric Grove.   It’s only 3.5×4.5 inches and a half inch thick.   I don’t carry this myself, but for someone who’s new to this whole bike repair business, it’s really helpful to have. A future blog post will cover this book in detail.
First, I researched. I looked at Amazon’s top-rated products and their user reviews. Then I consulted Bicycling magazine, Gear Junkie, Bike Radar, Outside, and the occasional bit by Lennard Zinn via Velonews. I also found some worthwhile discussions at Bike Forums. Then I spoke with four experts, Ramona Marks, Scott Karoly, Cari Z, and Alison Tetrick, riders from all across the spectrum, who tour, repair, and race.

The retractable tube is stored inside the body of the pump when not in use, and it can attach to either a Schrader or a Presta valve, the two types of valves you’ll see. Some pumps can accommodate only one type, making them less universal. Toggling between the two is simple, which can’t be said of other models with itty parts that require nerves of steel to handle on a good day, let alone while wearing gloves, crouching in the wind, oblivious to the sewer grate a few feet away.
Be organized. “I like having everything be really small and super organized. I put all of my tools in CamelBak’s Tool Roll. It’s got little compartments, and I can separate tire changing stuff in one place, stuff like extra pedal cleats or an extra derailleur hanger in another, and it all rolls up into this tidy pouch. If I do have a repair, I can pull that one thing out and lay it out on the ground and it’s easy to work.”
One key difference, that you can see in the photo, is that the BV uses buckles instead of Velcro on the straps that attach the bag to the underside of the saddle, something much more important than it may seem. A pair of bike shorts (or any shorts) will shred quickly if they’re rubbing against that tiny bit of Velcro protruding from the side of the bag, and it’s sure to destroy expensive sweaters and gym clothes if you stuff the bag into your backpack or messenger bag.
These are some great ideas, especially the simple ones like bringing a garbage bag. That’s something so easy and cheap that it’s easy to forget entirely, but as you say, it can make a huge difference in the right circumstances. It’s also good that you discuss some minor bike repairs. That’s another thing that can salvage or destroy your ride. You want to be as prepared as possible for the best possible experience.
Basic first aid supplies:  A few bandages of varying sizes.   6 Aspirin, or other OTC painkiller of choice.   A few alcohol pads in sealed foil packs, useful for cleaning grease off grease and grit off of the bike, and also cleaning cuts on yourself if you take a spill.  1 day supply of any prescription drugs you need to take regularly.   Wrap these up in tinfoil and tuck away.   It might just save your day.
The fabric attachment system is low-tech, but that seems to be helpful, as it can adapt to seat rails of different widths. One fancier option you might see on more expensive seat bags is a quick-release mount that you install under your saddle. But those have a fixed width, and therefore can fit under seats with only those exact specs. Brooks saddles, for example, are too wide for these mounts.
It’s both surprising, and not, if you think about it. The way I’ve usually seen it happen is first the rear tire goes flat, then the front one. My theory is that both tires went through the same pile of glass/thorns/metal bits and they both picked up junk. the reason for the flat occurring on the back first is because there’s more weight on that tire, so the offending article works its way through the tread more quickly.
The thumb test is the fine art of pressing on the tube with your thumb to see if it’s inflated. During testing, I took a pressure reading out of curiosity, and to the touch, road tires feel fully inflated around 30 psi. How pathetically sad—30 psi!—when you’re probably trying to reach at least 60 psi on a mountain bike, 70 or more on a hybrid, and it only goes up from there.
There are patches that don’t require vulcanizer—the infamous peel-and-stick. One brand, the Park Tool GP-2, has some genuinely enthusiastic endorsements, so we tested it. I applied Park Tool patches to four different tires, at three different psi levels (60, 90, and 120). Three of the four didn’t hold—two released within minutes. The fourth deflated overnight. I redid the test, but repeated a second time, they all leaked within a day.
There are two major types of headset- older, threaded headsets that have a quill that drops into the stem of the fork creating an interference connection, and newer threadless headsets that the stem is bolted and clamped on to. Flat handle bars are preferred by off road cyclists who can ride in a more upright postion whilst still having the controls at their fingertips, whereas drop handlebars offer more cycling positions and are favoured by road cyclists who typically spend more time in the saddle. The controls attached to the different styles of bar are operated and maintained in different ways.
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