Not THAT old. Oldest bike I had ever ridden is a 1923 Indian Chief, V Twin 1000 cc engine, side valves, 3 speed transmission. Hardtail with leaf spring front fork. Not as bad as one would expect apart from old style beadless tires. On a stretch of quality surface it´s absolutely lovely.
Oldest for me was a 41 Harley 45 c.i. flat head 3 speed tank shift that belonged to my father. Oldest I have owned was a 1949 61 c.i. Harley EL panhead 4 speed tank shift that I converted to hand clutch foot shift.
The oldest bike I've ridden was a '38 Ariel Square Four. IIRC, they were around 1000cc. My boss at the time had it, and about a dozen other antique bikes in a shed in his backyard. I helped him get it running back in the early 80s.
No, but I would if the chance came up. Otherwise, even if the bike was not ride-able and seized up with rust, I would pull up an old wood chair, kick back with some Alberta Premium and worship the bike.
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By the way, today I don't see too many street bikes on grassy plains and hill sides as these wonderful photos suggest.