To pick out a town, check the population. Indexes at the back map books often give population figures. Also keep in mind college and university towns but remember that the population and perhaps your audience numbers will be significantly affected by the school year. Even if a school has a summer session, some of your smaller colleges will not have a large on-campus population during the summer months.
If this seems like too much work, start hanging out with touring bands that play the same venues that your band does. They can be a wealth of information about venues, towns and even accommodations in each area. Select bands that attract similar audiences to yours so that you know there is at least one venue in a town for your type of music. The "circuit" of clubs is usually well known among road warriors.
Let's say you've picked out some potential towns along the way to and from your destination. You now need to find and select venues. As with selecting more towns than necessary when pre-planning your tour, also select more venues. This is a time-intensive process where you'll have to spend some time talking to other touring bands, researching and contacting clubs, etc. Personally, I find talking to other touring bands a good indicator of possible venues. From other musicians, you get more personal information (the inside scoop) on clubs, their owners and possible contacts. This kind of intelligence is just not available in a club or venue directory.
If you didn't get a chance to chat with a particular band that just played your area, try their web site. Often bands with list venues and dates on their web site. Although this won't give you that club intelligence, it will at least provide a starting point and from there you can use the Internet or a musicians directory to obtain more information on a club, its manager, sound and lighting information, capacity, etc.
If you must use a guide, I'm partial to the Musician's Guide since it is updated more frequently than the annual directories and a lot can happen to a club in a year.
Now comes one of the biggest challenges if you're doing your own booking - getting a venue to set a date for a band that has never toured before. I have written a previous article about getting booked for a local gig but when you are talking about an out-of-town date, multiply these efforts by at least hundred. We'll look at some strategies for getting out-of-town bookings next month.
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