John Harper wrote:

The answers so far seem to define challenging as "greatest risk if you mess
up".
That's a fair definition but if you go by difficulty of execution then the
NDB
to Siskiyou County, CA, (SIY iirc) looks like fun. I've never flown it but
it involves
a substantial dogleg at the NDB (particularly good if there's a crosswind)
as well as a death-defying descent rate on final.


Juneau, Alaska is no "bowl of peaches" either.

A fellow controller was riding jumpseat on a 727 a
number of years ago on a flight from Anchorage to
Seattle with intermediate stop at Juneau. The pilot
was enthused that this would be his first flight into
Juneau with VFR conditions.

There is a rather large dogleg to turn final and a
hill just slides under as you are, or just before,
making the dogleg. The Captain said that was the LAST
time he wanted to make the approach to Juneau in VFR
conditions.


Lou.