We have some pretty nice parks and paved walkways near our house that we frequent. Whenever possible I try to at least have the dogs jogging on non-pavement type surfaces. Running on hard pavement isn't good for humans or dogs in the long term. You can get sore joints from the high impact with the pavement. For the dogs there's also the abrasiveness of the pavement on their pads. Their pads are fairly tough, but will only hold up to so much. You also need to be careful of the temperature of the pavement that you're running on. While it may not be too hot or cold for you, your dog is definitely going to feel it with those naked feet!
Just like with humans, you want to build your dog up slowly so as to avoid injury. If your dog is relatively inactive, take it very slow and make sure that they are healthy enough to start this sort of exercise regime. You want to slowly build up your distance and speed over time and you want to make sure that you don't increase both at the same time. This can also lead to injuries. Another aspect to take into consideration is the length of your dog's toe nails. If your dog has long toe nails, cut them. Period. You can do serious and permanent damage to your dog's feet, tendons, ligaments, and legs in general, if you let them run around on nails that are too long (this goes for all activities and not just jogging). The general rule of thumb in my house is that if I can hear the nails clicking on our linoleum floors, the nails are too long. Which is why my guys get their nails dremmelled at least weekly. I'll probably do a separate post about this topic because it's a pet peeve of mine!:O)
One of my favorite places to take the dogs to jog around, are soccer and baseball fields. We are lucky to have many close to our house. The local parks and rec. department has a combination of two soccer fields and four baseball fields all in one area. You do want to be careful and respect the rules in your area though. Not all fields are dog friendly. Ours TECHNICALLY are not. However, I've talked to some of the grounds people and they don't mind us being in there as long as my dogs are on a leash and/or I'm VERY good about picking up after them (I'm not ashamed to say that I tend to use the "awesomeness" of my dogs to sway people, LOL). The #1 complaint people have about allowing dogs into certain areas is that owners are not good about picking up after their furry companions. It's just plain gross! But I digress! Running around in the sports fields allows you and your dog to run on a substrate that is "softer" and gentler on your joints and also cooler on both of your feet. Just compare how hot things feel when you're standing on dirt/pavement compared to standing out on nice grass! Another benefit of the sports fields is that there are often drinking foutains, bathrooms, or water faucets around for a quick drink or cool down.
As far as what distance you think you should start your dog out on? That's really up to you. No one knows your dog better than you do. But I definitely recommend erring on the side of caution for at the first couple of weeks. And if you really want your dog (and yourself if you're not already a runner) to adjust to the new routine, I recommend trying to fit in at least 2-3 runs per week.
And of course, always take into consideration the type of weather that you're running in. Running in the heat of the day is no good for anyone, least of all your buddy with the fur coat on!
Here are some pictures of the dogs, my mom and dad, and I at one of the 5k's that we've done (another GREAT activity to do when you and your dog are ready for it!).:O)