I just moved back to Billings after 7 years. I used to ride year round as long as there wasn't ice or snow on the road. I was always nervous about the cars sliding around. I would usually ride down to 20 degrees F. Billings is in the banana belt of Montana. Sometimes its 20 degrees warmer then elsewhere in the State. (yeah, so much warmer when it's only -20 degrees vs. -40 degrees). I believe Great Falls may stay colder then Billings.
I've been back in Billings 4 months now and it's been an unusual wet May. It's been up to 80 degrees earlier this month and last Saturday it was 32 and had snow on the ground. I've been wimpy and not out riding in the rain. Suppose to be getting to the more normal temps now, mid 40s at night and 70s during the day. It does get in the 90s during the summer. A dry heat (still hot, just dry), much better then the humidity back in DC. In the winters we do get Chinook winds that will melt/dry up the snow so we end up with no snow for periods during the winter. You can always check out the Icebike website (
http://www.icebike.org/) for biking in the winter.
Montana's a great place to live.
Good Luck, John