Normally my highschool runs their long runs at a city park, with some decent trails in the woods and around the soccer fields (5 mile trail, 3 mile trail, 3/2 mile trail around fields, 1 mile trail in woods), but I'm looking to do something different.
Recently, in the neighborhood next to my school, I discovered a trail through the outskirts of it that continues under a major road. I haven't gone further, but looking at the satellite images, it appears to follow a creek for a few miles in the woods before diverging two ways, north and east, and following the separate creeks for at least 5 more miles. It is unclear if the trail is easy to follow at certain parts of the trail, as trees block the view, but I am eager to find a new running route. I will bring at least one friend along, but not the whole team as I don't want to be responsible if a freshman gets lost. What else would you recommend? I live in the suburbs of a major city, so I'm not too concerned with being unable to find may way back, although it may take awhile if I get lost in the middle of the trail.
What would you recommend taking?
Also, as for a watch, would you recommend I run for time, or turn on my garmin? Running for time would be nice as I wouldn't be disappointed finding I "only" ran such and such miles, but since I'm mapping out a new route, garmin could be helpful.