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Join Date: Aug 2010
Location: Madison, WI
Posts: 11,216
Bikes: 1961 Ideor, 1966 Perfekt 3 Speed AB Hub, 1994 Bridgestone MB-6, 2006 Airnimal Joey, 2009 Thorn Sherpa, 2013 Thorn Nomad MkII, 2015 VO Pass Hunter, 2017 Lynskey Backroad, 2017 Raleigh Gran Prix, 1980s Bianchi Mixte on a trainer. Others are now gone.
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Where are you located? If you wanted to do the Glacier Waterton loop, that is a bit longer than 300 miles but the weather should be good in Aug.
But if you are out east, a lot of time gets consumed by traveling to and from Montana.