When planning a trip to the North East I came up with some bizarre routes suggested by the National Rail Enquiries website, but I've just come across this (last service from Carlisle to Whitehaven) which takes the biscuit. It declined to offer a fare though...
21:51 Carlisle [CAR] Glasgow Central [GLC] 23:04
23:29 Glasgow Central [GLC] Westerton [WES] 23:44
23:56 Westerton [WES] Preston (Lancs) [PRE] 04:29
05:22 Preston (Lancs) [PRE] Whitehaven [WTH] 08:09
That's 10hr 18 mins
Try it yourself. Carlisle - Whitehaven, depart after 21:00 on a weekday.
The last direct service leaves Carlisle at 21:50 and takes 1hr 15mins which makes it even more ridiculous.
21:51 Carlisle [CAR] Glasgow Central [GLC] 23:04
23:29 Glasgow Central [GLC] Westerton [WES] 23:44
23:56 Westerton [WES] Preston (Lancs) [PRE] 04:29
05:22 Preston (Lancs) [PRE] Whitehaven [WTH] 08:09
That's 10hr 18 mins
Try it yourself. Carlisle - Whitehaven, depart after 21:00 on a weekday.
The last direct service leaves Carlisle at 21:50 and takes 1hr 15mins which makes it even more ridiculous.