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Hiking with the Guide
The best suggestion for how to hike with the guide is to print out whatever sections you are planning to hike. If you are planning a thru hike, you probably don't need to print all the sections, and you probably don't want to carry that extra weight. Instead, stop in at a library to print out the next section or two. Not only will you only have to carry a section or two at a time, but by checking in at the library you will be able to see all the new information that the hikers ahead of you have added. Did the speedy guys in front of you find out the next hostel is closed? Now you won't have to hitch 20 miles into town to find that out yourself.
Print out the sections, and bring a writing utensil. As you hike along, write down any notes on the guide that you think might be useful. The next hiker probably doesn't need to know every flower and tree, but if there is a significant enough tree that can be used as a mile marker (i.e. something everyone would recognize as they pass it), then write down the landmark and the mileage on your printout. Then, when you get internet access, you can add the new information to the guide.
Think about water sources, camping spots, landmarks, viewpoints, etc. What did your last guidebook have in it that you thought was useful? Could TrailGuideWiki benefit from this type of information?
Towns are probably the most changeable aspect of long distance hiking. While we are off in the woods enjoying ourselves and ignoring the so called 'real world,' that real world is changing. Stores open and close, prices change, and things just generally happen. Add whatever you can to the guide. This is especially convenient since you are likely to have internet access in town as well, so you can update things right away.