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You can dig around online to find bike trails and paths. Multi-use (pedestrian, bicycle, rollerbladers, etc.) paths have complex etiquette and can present serious traffic hazards. Go slow, be prepared to stop, look around before changing direction and try to clearly communicate with those around you what you are going to do before you do it.
When you aren't on a trail, you're either going to be in the travel lane, on a shoulder, or on the sidewalk. In all likelihood, you will be doing a little of each. Take the time to plan each route ahead of time, and read a little about how to handle some common danger areas.
If you decide to ride exclusively on sidewalks, remember that bicycles freak out animals very often, cyclists can kill pedestrians (especially children), and every driveway is an intersection. If you travel at a pedestrian's pace you are unlikely to cause or find serious trouble. Think a jogger's pace when sightlines are good and there is no one else on the sidewalk (6 mph), a pedestrian's pace when there are other people nearby but they have stepped off the walk after seeing you (3 mph) and get off the bike and walk it if you are sharing a sidewalk with children, animals or other pedestrians who are not looking at you and responding to you. Comply with any local laws regarding not riding on sidewalks in certain busy areas. Walk your bike across streets, using marked sidewalks and signals whenever possible. If in doubt, hop off and be a pedestrian; you know how to do that already.
Wikipedia on Vehicular cycling, which is considerably saner than other commonly available summaries of vehicular cycling.
Please do not let this page scare you away from ever riding your bike. Do let it remind you to stay within routes and areas that you know how to be safe in. And do not let someone else bully you into taking a route you are not prepared for.
The idea of a walkable neighborhood involves useful things being within a mile of where people live: coffee shops, bars, libraries, shops, restaurants, movie theaters, schools, etc. While there is as yet no bicycling equivalent to WalkScore, you can apply the same principles modified for bicycling. In general, it is 2-3 times more tiring to walk a given distance than it is to bicycle that distance, so a bicycle ride of 2-3 miles is roughly equivalent to walking a mile. The major downside with bicycling is the problem of securing your bicycle at the endpoints of your journey.
The major takeaway for recreational cyclists is that they should not go more than 3X further on a bicycle trip than they would be willing to walk. Thus, if a three mile walk is your limit, you should not go further than 8 or 9 miles. And while walking downhill is easier than walking uphill, cycling downhill is stunningly easy, so if your trip out is downhill, turn back sooner than you think you should, as it might be much more difficult returning than you realize.
When you look at statistics from countries like the Netherlands and Denmark, or read about people who live there describing their daily bicycle trips, two things stand out. First, most trips are under a mile or two long. Second, most trips are taken at an average speed of 8 mph or less. This is true for their daily trips, and for their daily average over the course of a year. Don't let the Tour de France, or hearing about some enthusiast's "century" skew your expectations. It is reasonable to think that a five mile bicycle trip is on the long side.
You can run errands on your bike.
You can transport small children on your bike.
When you've got enough confidence to deal with occasional traffic in a subdivision, and have some confidence in your ability to escape whichever is busier (the sidewalk or the street), load up your bike with whatever kids and/or cargo carriers you intend to use (but without the kid or cargo) and ride the bike to make sure it still works like you are used to. There might be loose straps, knee banging, etc. Get used to your setup. Then start adding kids and/or cargo and practice until you have confidence.
Practice with your locks at home. It'll be hard enough tracking down an appropriate place to deploy the lock at your destination. You really don't want to be figuring out how to use the lock while managing the kid as well, possibly while amused bystanders are trying to chat you up about your bike and/or cute kid.
If you're going to run errands, I'd suggest separating the kids/cargo first (errand without the kid, or go some place with the kid but no cargo), before tackling them simultaneously. A loaded bike acts differently, and wherever you are going is almost guaranteed to be busier than a quiet subdivision. And ideally you should run the route and figure out where you are going to lock up without any pressure to complete the errand, and w/o kid/cargo on the bike. For one thing, if you've only driven the route, you may or may not have noticed what the hills are like (what hills? what do you mean, what hills!?!).
Don't add more than one kid to the bike the first time you put a kid on your bike. Try to have another useful adult handy when you first attempt to put a kid on your bike. Make sure the kid is awake and in a good mood. If the kid is unhappy, try again later; you don't want bad associations with the bike. With an older kid, it becomes important to make sure they understand not to lean way out to the side. Make sure they can't undo the buckles by themselves (the Bobike buckles are great for this). Have and use an adequate kickstand to help stabilize the bike, but do not rely on it completely (do not walk away from a kid on a bike).
Your first trips with the kid should be flat and short, then with a little uphill and short, then a little downhill and short, then you can start adding distance. You'll likely find that unevenness of surface is different with kids and/or cargo. With very little children (about a year), smooth surface is very iportant to avoid joggling them more than they can compensate for.
Your rescue arrangements when you go out with the kid will need to include appropriate car seat(s) for the kid(s), if you aren't walking or taking public transit home. You can generally walk a bike home even with a kid on it, with a flat, if you can walk that distance at all.
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Copyright 2009, Rebecca Allen Created: July 10, 2009 Updated: July 10, 2009