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A walk to Stirling train station, to then catch the 1408 Scotrail service to Montrose arriving 1548 (Thursday).

Lancing.

Think that's right, but not all at the same time, though?

Standard class £36.90 Advance Single (route "LNER & Connections"). Restriction code is actually 'GC'. (Valid on London North Eastern Railway and connecting services. Seat reservations are compulsory). https://www.nationalrail.co.uk/ticket-types/validity/gc/ So, is what the OP has asked...

@jadmor. What ticket type is this? Advance? Super Off Peak? Other? And are you travelling to Kings Cross? Also, how much did you pay? Was there any railcard discount?

Kettering.

Off Peak Return (Liverpool Stns to Cheltenham Spa) is £102.80 in Standard Class, route "Any Permitted". Would offer a degree of flexibility. Travel at or after 0930 during the week. Or it's £37.00 + £52.00 (total = £89.00) for Off Peak Return tickets, if splitting at Stafford, noting that...

We can then get the 2145 Scotrail train service to Ladybank, arriving 2244 (Still Monday evening).

@harry241. You could always consider taking out Royal Mail redirection. https://www.royalmail.com/personal/receiving-mail/redirection Not cheap, it's £39.50 for up to 3 months, or £58.50 for up to 6 months, but it's an option, and likely better than you being taken to court and not knowing...

Sandplace.

At York, one can then change trains for the 1832 XC train service to Berwick upon Tweed, arriving 2021 Monday.

Tamworth.

You'll likely be asked to pay all the incorrect/underpaid fares, plus a three figure sum towards the train company's investigation and admin fees. This is not a fine. Only courts can impose fines, and you'll of course then have a criminal record if found guilty, which might just be for the one...

Short walk to Manchester Victoria railway station, and then we're all aboard the 1443 Northern train service to Blackburn (via Bolton/Darwen), arriving 1534 Monday.

So noted. Henley to Maidenhead is currently something like £8.50 for an Anytime Day Single, Datchet to Windsor and Eton Riverside is £2.60 and Maidenhead to London Paddington is, I believe, £15.70. You'll know just how many journeys were made without paying the correct fares / inappropriate...

The £809 fare seems to be 2 x £404.50 Anytime 1st Class singles. The £297 fare seems to be 2 x £143.50 1st Class Advances (routed AWC&Connections) so booked trains only.

@ottrainman97. If you engage positively with the train company's investigation team, reckon there's a decent chance of you being offered a so-called "out of court" settlement and so avoid being taken to court. That's not an absolute guarantee, though, as they hold all the cards! By all means do...

Indeed. If the Thameslink train in question is the 0241 Northbound departure from Three Bridges which calls 0336 at London Blackfriars (0344 from London St. Pancras), then it won't arrive into Bedford until 0459.

@keysersoze. Welcome to the forum. So, basically, you got the train from London Liverpool Street to Stansted Airport, and tried to exit at the airport station using a less expensive ticket only valid from Bishops Stortford? Why do you think that's o.k. and that you shouldn't be liable?

Who can say? Depends on how positively you engage with GWR's investigation team. If the journeys in question were from, say, Reading in Berkshire to Central London, the undiscounted Anytime Day Single is currently £30.60, for each one-way journey. So 50-75 similar journeys, and you could...