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?
On a very sunny Saturday I had a rear spoke break - you can imagine that no shop was willing to promise a quick repair! I was so fortunate to find this shop and will come back - Andy not only told me to come down and he'd get it fixed, he had his assistant work with another couple while he measured, cut to the right size, installed and trued the wheel while I waited! It was awesome, and the whole place had a great feel and good people. Best of all he charged a very fair $20 for all that work - I would have paid a premium for the quick service! After experiencing lots of attitude at other shops and poor service, this was a real find. I hope you will check them out, they have a great selection of bikes and accessories too! Good people and good craftsmanship should be rewarded.
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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!
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!
Don’t rely on others. “People need to recognize that now there are different cassette sizes, so there are different chains depending on what gear you have. A lot of people are like, ‘Oh my friend is always prepared they always have the stuff, I’m not going to bring anything.’ All of the stuff now is very bike-specific, and you have to have your own package of stuff.”
Every person who considers themselves a cycling enthusiast should know how to do at least some basic bike repairs. This is not just to satisfy an unwritten standard of being a bikehead, but because it has a lot of practical implications as well. It can make the difference between dealing with a minor issue quickly on your own or waiting a couple of days for a busy mechanic to squeeze you in. Moreover, in the long run, doing the dirty work yourself will save you a lot of money.
If you’re going to use the chain whip you just made, you’ll also need a way to get that cassette off. A lockring remover is a must-have; unless you use one of the shady removal methods I’ve seen on the internet—which I wouldn’t necessarily recommend unless you don’t care much about the condition of the wheel after you use them. I recommend Park Tool’s iterations here that cost about $6, but you’ll need to buy the specific one for your brand/type of cassette. (By the way, I’m assuming you already have an adjustable wrench laying around somewhere to use with this tool. If you don’t, well, you’ll need one of those too.)
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!
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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