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The registration of the car looks like DBD 78C a 1965 Northampton registration.
So that dates the pics to 1965 & later, it may be a rider in the Northampton area as in those days cars did no generally stray far from there original county of registration. The trailer looks a home made affair made from an invalid carriage, an Invacar maybe.
The rider is probably a local privateer rather than a works rider.
looking at the picture of the guy i wonder what else he had in the row of sheds behind him,just a thought there may be an original greeves in there just waiting to be discovered,it does happen i found mine in a collapsed barn where it had lain for fourty years
The bike is a 24mx4c short stroke challenger in uk spec, Only around 32 of these were made, they were officially a 1968 bike, but some left the factory in late 67 I believe. looking at the bike it looks totally original, so it must have been quite new I suspect.
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