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?

To pick the right size bicycle, you want to measure your height, and specifically your inseam (inside leg), in proportion to the size of the bike frame. The inseam measurement determines the seat height, or the “stack.” Next, you must calculate the “reach,” which is the horizontal distance between the bottom of the frame and the head of the bike -- or, in layman’s terms, the distance between seat and handlebars.
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.
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.
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.

We rented a tandem bike from here for an hour, and they were super chill! We dropped by on a Sunday and decided to go eat first; Andy, one of the owners, was awesome about holding the bike for us while we went to eat before renting. We enjoyed our ride for just over an hr, but Andy was also super relaxed about our return time and only charged us for an hour. We had a fantastic time and would definitely recommend renting bikes from here!

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.

To pick the right size bicycle, you want to measure your height, and specifically your inseam (inside leg), in proportion to the size of the bike frame. The inseam measurement determines the seat height, or the “stack.” Next, you must calculate the “reach,” which is the horizontal distance between the bottom of the frame and the head of the bike -- or, in layman’s terms, the distance between seat and handlebars.

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.

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.
Main types of bicycles are road, mountain, commuter/comfort and fitness bikes. There are more specific types and other names for bike types within that, such as urban bikes (same as commuter bikes), cruiser bikes, dual-sport bikes, hybrid bikes, fixed-gear bikes, cyclo-cross bikes, adventure road bikes (aka  all-road bikes, gravel bikes), road bikes, touring bikes and specialty bikes, like BMX.
Good bike repair stand. I can't say "great," because it arrived with some small plastic pieces broken. These are small pieces that go between the legs and the supports for the legs to act as a sort of buffer to prevent metal to metal scraping. They are just too fragile, it seems. 3 out of 4 legs had these broken upon arrival. However, these are really only "nice" to haves, not need to haves, and they don't really detract from using the stand in any way. Once you have the stand set up, you don't worry about these at all. The main clamp holds the bike well, if you take care to balance the bike properly. The bike may tilt in the stand if you don't balance it - there is a weight limit to the clamp. I like the included tool tray, but I wish it was more adjustable in height (it is essentially fixed in one position). And the tray could be larger. Otherwise, I am quite happy with this stand. I have worked on several bikes using it, and assembled one out of the box. It makes the job of doing things like adjusting brakes and indexing derailleurs so much easier. The price of this stand is excellent considering the quality.
More than any other tool in the kit, a reliable lever makes changing a tire easier, especially if you have road bike tires, which are difficult to remove. However, throughout testing, levers seemed to be the one item more prone to failure and poor design than anything else. For example, I found a random orange lever floating around my basement and I threw it in the test pool for fun—it seemed solid enough … until I began prying at the rim of a tire. It bent directly in half, slowly and smoothly, like taffy, and then was boomerang shaped forevermore.

Whether you ride a single, 7, or 10 speed bike or anything in between, you will need a slightly different chain. The major difference is that they come in varying widths to accomodate the different spaces between the gears, but quality of construction is also a factor in choosing a chain. Inspecing the chain should be a part of your regular cycle maintenance procedure- It’s important to keep a chain well lubricated, but oil will also attract dirt and so different oils for specific riding conditions are available. Remember to clean your chain regularly to get the longest life out of it and the gears.
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