In article .com,
gwengler wrote:
To my knowledge, in the US one must file an alternate IFR airport
regardless of the weather if the destination airport does not have an
IFR approach. Can someone please quote me the FAA regulation where
this is actually spelled out? Thanks!

91.169(b). It's a little confusing, since it's worded as an
exception. If your destination does not have an SIAP, it doesn't meet
the requirements of the exception clause.

Actually, I just noticed a detail I never saw before. It says:

"... a standard instrument approach procedure to [...] the FIRST
AIRPORT OF INTENDED LANDING" (my emphasis).

So, it seems like I could file "HPN -D- BDR D/010 -D- BOS",
i.e. "White Plains, direct Bridgeport, ten minute delay (not sure if I
got the flight plan symbol right for that), direct Boston" and as long
as BDR doesn't doesn't require an alternate, I don't have to file one
for the BOS leg either, since BDR is my "first airport of intended
landing".

This seems rather stupid, but if you read the reg literally, that's
what it says.