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.
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I bought this book to supplement "Anybody's Bike Book" because I always like to get a second opinion. This book uses photos extensively rather than drawings as in the other book. They are well composed and quite helpful providing additional detailed information in a clear, conciseful manner. Information is provided in heirarchy format and geared from initial purchase to daily maintenance of my two wheeled friend. Good book!
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?
Otherwise, this tool should serve the average commuter well. Specifically, we think you’ll find the size 4, 5, and 6 hex keys, extremely common sizes in bicycles, very helpful. They’ll adjust seat-post heights or let you remove the saddle entirely, or tighten a loose stem that’s always rattling apart. The Phillips head will tighten loose bolts on shoe cleats or the rear derailleur. The most common use for the torx would be adjusting disc brakes if you have ’em.
We focused on tools that would be useful to a commuter—someone trying to use a bike as a functional way to get around town, as opposed to riding recreationally (road biking and mountain biking). That said, it’s a wild and wooly bicycling world out there, and the streets are packed with so many different bikes, all shapes and sizes, new and old. Customizing your flat-fixing kit has advantages over buying a preassembled kit that always contains a tool (or two or three) that’s a piece of junk, or you don’t need. Or it’s missing something you do need. If you build your own kit, at least you know everything works. And you can add only what’s necessary for your specific bike without ending up with stuff you don’t need.

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.
Patch kit:   Patch kits are easy to use, light and compact, and if you get more than one flat on a ride (it happens more than you’d expect), it can save you when you’ve already used your spare tube.   Plus, on a rear wheel, patching a tube can be faster than replacing it, as you can often do this without removing the wheel at all.  Another upcoming post is going to show you how to patch a tube.
It includes nine tools: seven hex bolts, one torx bolt (the star-shaped one), and a Phillips screwdriver (also the star-shaped one). Like Peter says in our guide, if you have a newer mountain bike or road bike it pays to take a quick look at what types of tools you need, as torx bolts are becoming more common. And a quick glance at the bottom of your shoes or derailleur bolts will confirm if a Phillips head is the right choice.
Mountain bikers are in different world of repair entirely, one that borders on the comedic absurd. It includes large pumps designed to fill up big, fat tires that squish over things, and a medley of assorted slimes meant to be injected into tubes or tires. In that world, the number of days it takes you to fix your tire and return from the wilderness is a badge of courage—bonus points if you’re bleeding—and we’re guessing that’s not what you’re going for next time you set out for groceries.
On the other hand, an on-bike repair kit will be a much smarter selection of tools that you are most likely to need. You should figure out the type of screws that are fitted on your bike and the things that are most likely to go wrong on a ride. Address only these things so as not to burden yourself too much with unnecessary stuff. Moreover, there are bike repair kits used on long rides and those used on shorter rides. The longer the ride, the more tools, and spare parts you will have to bring unless you want to have a very long hike back 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.
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?
This is a very basic book and unnecessarily repetitive in sections. It does introduce the reader to the basic nomenclature of bicycles and this is helpful when conversing with others. Unfortunately the repetitive sections were not replaced with chapters on 3 Speed in hub gear drives, or coaster breaks, or a chapter on Adult Tricycles and Tandems and E-Bikes.
These guys are awesome.  After work, I got to my bike to discover my back tire was completely flat.  It had a slow leak, so I was able to pump it up enough to make it to their shop.  I got there 10 minutes before closing and they were able to fit me in.  They replaced my tube and picked all of the glass shards out of my tire.  Awesome customer service and they saved me from having to do this myself in the dark and the cold.
The Bicycle Repair Shop does rentals by the hour or by the day. They have reasonable rates. They have solid, lightweight hybrid bikes so you can tackle train tracks and brick streets and hills. They also have road bikes for the more experienced. You can reserve online in advance. You get a helmet and a lock with your rental. The staff in the shop are friendly and will suggest routes and point out hills if you're new to the area. And believe me these hills are no joke!

We like, and recommend, the Crankbrothers Speedier Lever. If you have to pick only one, go with the Pedro’s, but if you want a backup or have some hard tires to unseat, Crankbrothers is a great choice. It’s only one lever (as opposed to a set of two, like the Pedro’s) and it’s longer, so we didn’t pick it over the Pedro’s for portability reasons. But it’s an excellent tool. It has a wide handle you can grip with your whole hand. Like the Pedro’s, the tip is the right size and shape to prevent slipping and stay in place, and the shape of the handle happens to protect your knuckles if you do slip. Even in situations where I didn’t need it, I liked having it because it made me feel like a pro.

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.

Now you might be wondering: “I’m carrying a tube; why carry patches at all?” As insurance for the unforeseeable. Wirecutter senior editor Christine Ryan admits she didn’t use to pack them, but said, “I’ve regretted that decision when I’ve had a flat on a ride, used my spare tube, and then, half an hour later, had a second flat. Also, lots of people aren’t very good at figuring out—or don’t take the time to figure out—what caused their flat and remove the cause: thorn, eensy bit of glass, whatever. Then they promptly have a second flat, and everyone else laughs at them.”
It is a good solid stand made mostly from heavy metal, but it does have a couple of problems. (I will use part names from the instructions to explain.) First, the clamp between the "telescopic bar" and the "upright" is plastic. It arrived broken in the box. Whoever boxed it should understand that if you put it in the box broken, the customer will remove it from the box broken. I did not return it as broken because I was able to Gorilla Glue it back together and it works fine; it clamps tight enough to hold the telescopic bar in place. Second, the "bike support stand" (the horizontal bar at the top that holds the bike), when attached to the seat support does not grip tight enough to hold the bike in the position I set because there is too much weight from the front of the bike. The torque causes the bike to rotate until the front wheel is on the ground. That is not enough for me to return the stand because I seldom work on the front wheel and if I do I can attach the stand to the top horizontal of the bike frame. I think they could fix the problem by not making the "bike support stand" so smooth, give that part a sandpaper like finish or put rubber fingers inside the clamp so the part does not slip under the torque from the weight of the front of the bike. I might rough up the stand part with sandpaper, or put small grooves in it to give the clamp something to grip on to see if that solves the problem. Third, the clamp holding the bike frame even at full tight will not keep the bike from rotating around the frame. It is not enough for me to send the stand back, just a minor annoyance. The problem is there is smooth plastic trying to clamp a smooth metal frame. I think they could fix this by putting thin rubber pads in the clamp. I will probably run out and get some pads to try that out. I think it is a good stand for the price. The stand itself is made from much heavier metal than I expected. It is very stable with the four legs. I easily overcame all the issues so I kept it.
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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