I'd like to be prepared to handle most breakdowns on the run and equipped to properly maintain my bike at home. Does anyone have some recommendations on tools or equipment for either situation? Also, what about general bike maintenance? What do I need to do on a daily, weekly, monthly basis?

A lot will depend on just how prepared you want to be.

The most common issue you'll likely face is a puncture, and to fix a puncture you need tyre levers, a patch kit or spare tube, a pump, and perhaps a bit of patience. Depending on just what setup you have you may be able to get away without even using levers (I fixed a flat with Specialized Borough CX tyres with no tools at all, but really struggled to work with Schwalbe Marathon Plus tyres).

A basic multi tool containing a bunch of allen keys (not sure what you US folks call them - hex keys or allen wrenches?) will probably cater for most of what you'll need on the trail. I've never needed anything more complex than a pump and a couple of allen keys. Personally I like to carry a couple of loose allen keys as well on the basis an individual key is easier to work with than a multitool, simply because it's less cumbersome. A cross-head screwdriver is also worth having although I've never actually needed one in the field.

If you break a spoke you might be thankful for a spoke wrench to adjust the tension of your wheel to stop it rubbing. If you've got disc brakes you probably won't need to worry about that though.

You might want to take a few links of chain and a chain tool and maybe a couple of master links so you can deal with a chain breaking. I've never had that happen to me but I know people who have.

If you go much beyond that you have to decide where to stop. You could take some spare brake cables and shifter cables in case they break but unless you're into serious long-distance riding you might be better off learning how to improvise so you can get back to a decent workshop and fix it there.

The most important thing, by far, is to be able to handle a flat tire by yourself. If you can do that, you're at least 95% (probably more) covered. To do that I carry a spare inner tube (I don't like to patch on the road), something to inflate it with (mini pumps suck), and probably a set of tire levers. Practice at least once at home.

Beyond that it depends on how much of a worrier you are. If you have a good attitude, you're good to go. If you worry a lot, your bag of tools and spares will grow gradually heavier and heavier to match your mood.

I do no regular maintenance. During the course of each ride, however, I make a mental list of whatever needs to be done before I ride my bike again. As far as tools go, you'll be surprised at how far just a 5mm allen wrench will take you. Aside from that I'm an advocate of just buying tools as you need them which won't be very often. When it comes time to replace your chain, tool up for that. The first time you decide to overhaul your hubs, but the right size cone wrenches.

Agree with most of this, except that I clean the bike and clean and oil the drivetrain every once in a while (depending on how much I've been riding, conditions etc).

Depending on just what bike you have you'll probably find a 4mm and 5mm allen key will do most of what you need.

Agree 100% with buying tools as you need them. Otherwise you end up with lots of money spent on tools that never get used. I'll make an exception if I know I'll need a tool in the not too distant future and it's available at a great price.

The first "tool" you should obtain is knowledge. Get a good repair manual and/or visit the Park Tool's web site and sheldonbrown.com/harris and read up on various maintenance topics. If there is a bike co-op in your area, they are often an excellent source for hands-on instructions.

As to what to carry on the road, I agree that a set of tire levers. a spare tube (or 2) and a means of inflating it are the minimum along with the ability to use them. Beyond that a mini-tool with the common allen keys and, perhaps, a small chain tool will handle nearly everything you are likely to encounter on a ride.

Thanks for the tips everyone. I'll go pick up a spare intertube and some levers this afternoon. I've got everything else I need for now I think. =)

Here's a good maintenance schedule. This is for bicycles with adjustable bearings. Some sealed bearing systems are non-adjustable and non-maintainable.
https://www.seattlebicycleclub.org/me...intenance.html

Also pick up some metric allen wrenches in the Y wrench design.

ChrisBailey: Rather than a multitool, which has many sizes of hex keys you don't need, or a "Y" key which takes excessive space, I'd recommend you procure long arm "L" wrenches in just the sizes your bike requires. They are lighter than a multitool and take little space and you will only need a few. Make sure that the tire levers you get are stiff enough to do the job; I like to carry three. You will also need a wrench for the axle nuts if you do not have quick release skewers. A chain tool and a few spare links (like the ones you cut from a new chain) or a couple of master links may come in handy, for yourself or to assist another rider. A few heavy zip ties are handy for improvised repairs and take little room. Wrap the tools in an old rag or towel that you can use to wipe your hands with when you are done working. It is best to practice changing a tire at home to make sure that you have the proper, capable tools and to get some practice before you have to change one on the road, in the rain, when it is getting dark.

+1000.

Absolutely agree. The one thing you don't want to be doing is figuring out how to do a job when it's so cold you can't feel your hands, you're miles away from home, it's raining and the light is fading, and something is broken on your bike so you can't ride home until it's fixed.

Depending on where you are you could always call a taxi to take you home (or a friend with a big enough car) but that assumes you've got cellphone signal, a willing friend etc.

4mm hex.