I chose to test these four levers after eliminating everything out there that’s not appropriate for a roadside emergency kit. That includes metal levers. They’re durable, but according to touring cyclist Ramona Marks, “Metal tire levers are trouble. It’s possible to rip your tube even with the plastic ones if you’re not careful, so metal is out of the question, and you don’t want to put pressure against the wheel rim with a metal lever.”
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?

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.
Any bike that gets ridden seriously as transportation or on long rides needs at least a basic tool/emergency kit, and the knowledge to use it, unless the rider is always in a position to call a friend with a car or a cab when their bike needs a quick fix on the road.  If you never travel more than a few miles, this can be overkill, and calling a friend or a cab may be just the ticket,  but if you want to be more self reliant, this is something you should seriously consider.  This list may sound like an awful lot of stuff to carry, but really, it only weighs a few lbs and fits in a small, under-seat bag that comes off quickly so I don’t have to leave it with the bike if theft is a concern.  If you always carry a regular rack top bag, you can also just put all this in a small nylon bag and throw it in there, but I prefer an under-seat bag.
A multitool is a highly versatile piece of repair equipment that can address most of your maintenance needs. Ideally, you should use it before a ride to tighten and adjust everything properly, but sometimes it’s necessary on a ride as well. If you encounter a loose screw, realize your saddle height is not right, or that your brakes need tightening, you will be happy to have it.
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!
Friction gear systems are a lot simpler to adjust, because the movement of the derailer cable can be modulated as you ride, every time you change the gear- they require less cycle maintenance. Modern index shifting systems are a little more complicated because each ‘click’ must release the exact right amount of cable to allow the derailer to move the correct distance to move the chain from one gear to another. Setting up and adjusting a derailer is not difficult and requires only basic tools, but there is a methodical procedure to follow.
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