There's always the possibility of online or catalog sales from the "official" gift shop...I'll bet not many posters on this board would complain about receiving ANOTHER C&TS sweatshirt (or tie) for Christmas.
Unfortunately, this is the kind of thing that needs to be in the works about 4-6 months in advance (to allow time for adverts, catalogs, etc) to work well. It also requires someone to be there to answer the phone... perhaps at weird hours. (I've gotten several at 3am, some were from drunks telling me that you could buy a pickup for about the same price as the OS (4-3/4" gauge, live steam, ready to run) 4-8-2 locomotive... but some were from customers in Europe or Asia with nice sized orders).
As for winter stuff on site, you'd have to work with the communities to make any money at it. Probably the only potential money makers would be limited to short excursions during a winter carnival, or Santa Claus runs a few weekends in late November and December.
...of course, you could always try to find some developer willing to build a gazillion dollar winter sports complex that was accessable only by rail.