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Suppose I have a Freedom of the Severn and Solent. I’ve decided to travel from Worcester to Birmingham and I simply buy a single ticket for this part. However, if I want to then travel via Cross Country to Bristol, where do I buy my boundary ticket to ? CC is not routed via Worcester so it can’t be there, similarly my FOSS rover has validity further both than Cheltenham Spa?

A single from Birmingham New St - Ashchurch for Tewkesbury would be needed.

As one of your tickets is a Rover you don't need to travel on a service that calls at Ashchurch for Tewkesbury.

Condition 14.2 of the National Rail Conditions of aTravel:

Very many thanks for this.

If the journeys being made are Worcester - Birmingham and then Birmingham - Bristol, the cheapest way to add on to a Freedom of Severn & Solent Rover would be an Off Peak Return from Ashchurch for Tewkesbury - Birmingham New Street. Such a ticket is valid both via Worcester and direct.

There seem to be two types of ticket: NOT via Cheltenham and any permitted route. Guess I’d need the latter ?

There's only one Off Peak Return between Ashchurch and Birmingham.

£26.10 Any Permitted.

Although if you were buying a Single from Birmingham to Ashchurch the Anytime Day Single not via Cheltenham would be fine as you are not travelling via Cheltenham on that ticket. After passing Ashchurch for Tewkesbury you would be travelling on the Rover.

However, if your concern is more for cheapness than time taken, it would be better to get a return from Worcester to Birmingham for £9-30 and then take a train to Ashchurch or Cheltenham from Worcester. The fare is MUCH cheaper than going by Cross Country or from Ashchurch.