The Bootleg Trail is most used as a connector between a few of the trails on the northeast side of Tiger Mountain. Consisting of Upper, Middle, and Lower Bootleg, it leads from the Preston Trail to West Tiger 1, providing a more rugged and isolated option to West Tiger 1. Bootleg is a great route down from the Hikers' Hut on Tiger 1. As a connector trail, it does not have a trailhead but is well-marked on either end with wooden signs.
While this trail can be accessed year-round, navigation/route-finding skills are usually necessary in the winter, as snow can get deep on that side without the amount of foot traffic that the west side of Tiger sees, making the trail virtually invisible. End to end this trail is just over two miles and going east to west gains about 600 feet in elevation.
Its lack of easy access and moderately rugged terrain aren't a good fit for strollers or wheelchairs, but small children and dogs would be okay on the Bootleg Trail. There is one water crossing at the East Fork Issaquah Creek made easy by a tiny bridge. Closest parking is found off of I-90's Exit 22 in Preston near the DOT facility, or at the High Point Trailhead (Discover Pass needed).
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