check out Google Earth, you'll have to download this program, but it rocks. You can zoom in anywhere in the world, and see satellite images of ....well everything. Using this you can map out routes on streets, through parking lots, through parks on trails, cut through buildings, hop fences....well maybe a less complicated route but you get the picture, you don't have to stick to streets like a traditional mapquest would show you. You can even turn on layers that will show you where coffee shops are along the way. After you get a route picked out, you can go to
www.gmap-pedometer.com and figure out what the distance your route covers. Google Earth has this feature too, if you pay for all the features, but I just have the free version, 'cause I'm a cheapskate.
good luck.