Join Date: Jul 2007
Location: Helena, MT
Bikes: Specialized FSRxc Pro, Softride Norwester
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Helena has a couple of good bike shops, Great Divide Cyclery and Big Sky Cyclery. I've bought bikes at both. We've an active club http://helenabicycleclub.org/
with some great weekly rides and some organized, fully supported long rides; The Double Divide and One Helena Hundred are local-ish road rides in June and July, with the York 38 special MTB ride in August http://www.york38special.com/
There's other stuff as well, but you should find plenty to do on your own!
Plenty of great rides around the valley and up in the mountains; not a lot of snow in the winter, but it gets DAM cold. Switch to cross-country skiing from Thanksgiving to sometime in March and you'll be fine.
The city itself isn't any more or less bike-friendly than anywhere else. The major routes through town get pretty congested and they're tight, some not designed with even cars in mind.
Got any specific questions?