I am in from Chicago, IL!   Which bike should I bring?  Krampus or Raleigh Tamland?


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Have you seen this?
http://bikepackersmagazine.com/video-black-hills-expedition-2014

Also, if you get there early enough in June, there is a gravel race you could do.  Gold Rush Gravel Grinder.  June 6th. Good source for local trail info, I'm sure.

Look at #blackhillsexpedition hashtag on Instagram for some photos.

Ooooh, cool.
Anybody got any idea about snow in early June?  Looks like you don't get super high altitude so that should help.

I'm not from the area so take this is just an opinion from looking at the historical weather.  Snow is not likely to be a problem but cold nights and some rain are likely.  Wet conditions will make a few sections of this route unrideable but there are lots of bailout options throughout.

I really enjoyed this last year.  Scenic, challenging, and always an option to head into a nearby town.
http://blackhillsexpedition.blogspot.com

I have one and I love it.  It is nice to be able to take at least 1 bag easily off the bike.  That said, I am coming from a touring background and have gone the bikepacking bag route primarily as a way to force myself to carry less crap.  I don't have much experience off-road. My current set up is Tangle, Terrapin, Gas Tank, and front Panniers.  On a Salsa Vaya.