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Let me hazard a guess at dates: The Penny must be 1880's and the later one about 1905?
That's my guess knowing when he was born and what he looked like at different ages in pix where we have more clues about when they were taken.
One of my great uncles was apparently also pretty quick in the 30s, but we don't have pictures.
gbj_tester
Great pictures, both of them.
The later one, being well focussed, has excellent detail - is that bike a New Hudson?
It certainly looks as though your Gt. Grandad wasn't planning to hang about, with that big chain ring (50, 52 ?) and open side tyres. I also note that his saddle is a bit higher than the handlebars, so it's not a sit up and beg position.
In fact this bike is quite close to what I was trying to imitate with my Sunbeam roadster, although I've got a 44 ring and no aspiration to speed.
Let me hazard a guess at dates: The Penny must be 1880's and the later one about 1905?