A plastic garbage bag, or $2 disposable poncho:  Just in case of an unexpected downpour or getting caught out after dark.   More than once, I’ve gone for a ride on a beautiful day with a perfect forecast, not taken a jacket and had the weather go south on me.  Being able to cover up can mean the difference between just mild discomfort or a freezing cold, shivering ride home!
That’s a reality of all hand pumps—it’s really hard to get a tire up to pressure with these things. So another reason Lezyne pumps are so good is because you can actually keep pumping longer than any other brand we tested. With excruciating effort, we could get the Sport Drive HP to pump tires to 90 or 100 psi. It still wasn’t easy, but it wasn’t impossible the way it was with some other models.

Unlike floor pumps, most hand pumps do not have pressure gauges. To get readings during my original round of testing for this guide, I built a special rig involving simple hardware-store parts. But the experts I spoke to seem divided on the usefulness of gauges. Half thought they were unnecessary, added bulk, and drove up cost. Why do you need a gauge if you know 100 pumps inflates your tire? But the other half liked them, because the “thumb test” is notoriously inaccurate.
Let me go ahead and get the bad stuff out of the way. First of all, this stand is NOT the same level of quality as something you would find in a bicycle shop being used for the shop's repairs. it's quite a bit more flimsy, and the grip likes to rotate if you don't get the bike's center of gravity just right. The tool tray is also made out of a rather cheap plastic that can break easily at the rim. That being said, this stand is perfect for home users and makes mundane tasks like fixing a flat or cleaning the chain much easier. It easily holds my Raleigh Merit 3, and I don't worry about the thing falling even if the grip tilts a bit. The stand significantly shortened the time I needed to change an inner tube on my bicycle, and made me less worried about damaging something on the bike by jury-rigging a stand out of whatever I had lying around.
Change and a $20 bill:   In case your cell phone’s battery dies, it’s nice to still be able to use a payphone if you need to.   Also, the $20 is a great thing to have in case you lose your wallet or have some other mishap.   I’d rather be able to sit in a coffee shop or fast food restaurant when it starts raining while I’m waiting for my friend or cab ride, and a hot cup of tea or coffee or the beverage of your choice and a snack makes it all the more pleasant.  Just try to remember, this is for emergencies, and if you use it, replace it ASAP!

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.
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?
A pair of disposable latex gloves:  Not absolutely necessary, but good for keeping grease and grime off your hands during a repair.  Also, nice to have in an emergency when it starts raining and the temperature drops 20 degrees and you don’t have a pair of regular gloves.   Just keeping your hands dry and the wind from directly blowing on them makes a huge difference in comfort.

Broadly speaking there are two major wheel sizes – 700c for road bikes and 26 inch off-road wheels. However there are a whole variety of older, less common wheel sizes and of course fold up bikes have much smaller wheels altogether. Repairing a puncture is not an emergency! It’s a basic procedure that every cyclist should be able to to perform, but doing it correctly involves more steps than many people realise. Wheel building is often seen as the most artful skill in bicycle maintenance, and separates the professionals from the amateurs but that doesn’t mean you should consider it out of reach. Truing a slightly misaligned wheel is a cycle maintenance job that almost any cyclist can perform.
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