When is the trip supposed to begin?
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PS Any MUST see's or MUST NOT do's please feel free to let us know.
But if you go by yourself you need to be okay spending a lot of time in your own head. On the plus side, no constant negotiations on how far, or how fast, or where and what to eat, or where to stay.
All of the shops in town should be able to help you out, but as mentioned above, Hellgate Cyclery is very close to the Adventure Cycling headquarters and has great service. If looking for a shop with more product inventory, Missoula Bicycle Works is right across the river from downtown.
BTW, I'm leery of using "on-your left" announcements on some mass rides or on Rail Trails. There are so many inexperienced and inept riders there that their response is often to veer to the left which is exactly what you DON'T want them to do.
One way is to head north and pick up the Northern Tier to Whitefish, MT. Then due south thru Seeley Lake. Not the most direct, but very scenic.
Passenger rail service in this country, with the possible exceptions of the Northeast corridor (say Norfolk VA to Portland ME) and the Pacific coast from San Francisco to San Diego, has too low a population density and too much space between major cities to be economically feasible.
As a rail supporter since the late 1970s, I have seen a steady erosion of baggage services nationwide. Since many stops outside urban corridors have, at most, one train each day in each direction, it is prohibitively expensive to staff a station. For liability reasons it is risky to have people do their own loading. It's one thing on urban routes with raised platforms or low-level car doors to have cyclist bring their own bikes on board - - but to get a bike into a baggage car may involve too much risk.