This question is purely out of vein curiosity, as I’m not an aircraft owner. But if I were, flying to Alaska would definitely be on my proverbial bucket list, and among those places would be Unalaska. They don’t sell 100LL at Dutch Harbor. However, it’s only 155 nm straight-line from Cold Bay which does sell avgas, at cut-throat prices (Nelson Lagoon is only 225 nm and their prices are much more reasonable). I like to think this trip would be feasible in something like a Bonanza. I think even a C182 or Cherokee 235 could make it (pack some 5-gallon jugs of 100LL). I realize that this being Alaska, unexpected weather such as storms, IFR conditions and winds aloft could impede a flight straight flight to Dutch Harbor and back. Runway conditions and windy weather might also be a factor. This could be the reason why you can find videos of jets/turboprops visiting, but no single-engines. Perhaps there are also regs that forbid pistons from landing, though I didn’t see any on the AFD page or from a Google search.