The oldest planes I've flown in are EAA's 1929 Travel Air E-4000, 1930 New Standard D-25 and 1930 Pitcairn Mailwing PA-7.
The oldest I've had my hands & feet on the controls is EAA's 1929 Ford Trimotor, if a replica of the 1927 Spirit of St Louis doesn't count.
The oldest I've soloed is a 1931 Aeronca C-3