Dear JulieI am a Rupert Bear collector and I may be able to help with your query:-
The book you mention is:-
Rupert Colour Adventure Book c1950s containing
Rupert Gets Lost Again later renamed Rupert and the Circus Clown first published in 1926 in the Daily Express and drawn by Mary Tourtel and Rupert and Bills Aeroplane Adventure first published in 1933 and drawn by Mary Tourtel, Mr Bear has a horse and cart because in rural England in the 20s that is how people got around.
Hope this is helpful
If you wish to contact me my fax number is 020 8658 8498 UK
Regards
Peter