Fan trips and other special services

Fan trips were or are special charter trains not run for the general public. Have those ever been a regular occurrence in North America? Also, how about other special services with onboard catering and maybe side tours as well?

They were, until the cost of insurance became prohibitive. Friends of the 261 still run these up in Minnesota because they have a railroad willing to allow them. Most of the other railroads do not want the liability.

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Do you mean fan trips were a regular when insurance was cheaper? How about other special services, like those tours including a special train service (with onboard catering) and side tours?

Did any fan trips and do any current special services cross state borders (in the US) and province/territory borders (in Canada)?

Have any fan trips or any other special services in North America ever even crossed country borders, like the US-Canadian border?

Those other special services would be other charters or would be tours? Are there a lot of those in North America. It seems that less than half the railroads in both the U.S and Canada see scheduled passenger service, this could make North America quite an ample ground for charter and tour services?
Do sleeper train tours exist in either country?

Fan trips were or are charters; There were chartered by special interest groups with their own plans. Other special services are organised by some other kind of group, usually a preservation group, which decides where and when.

Other special services, while not scheduled services, do not count as charters.

Does the Friends of the 261 train run on lines that are not used by scheduled passenger services?

Could it be that no one here knows the answer?

Their recent trips have been on the TC&W, which clearly doesn't host Amtrak. But they've also run on the CP and BNSF, which do host Amtrak.

IIRC, the CN steamers that ran in 1960s crossed the border to run trips on the US side, but I do not recall any trips with passengers crossing the border. CP 2860 has run trips in US, especially for British Columbia in 1970s, but once again no cross border with passengers. Then there was the Flying Scotsman [LNER 4472] which toured US and Canada 1968-72.