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- May 29
James J. Hill
- 1916 – James J. Hill (pictured), American financier who gained control of the Great Northern Railway and the Northern Pacific Railway, dies (b. 1838).
- 1935 – The Milwaukee Road inaugurates Hiawatha passenger train service between Chicago, Illinois, and St. Paul, Minnesota.
- 1955 – The Norfolk and Western begins its conversion to diesel locomotive power from a purely steam locomotive roster with the purchase of eight ALCO RS-3s.
- 1984 – Canadian Pacific Railway (CPR) operates the last train over the railroad's Waltham subdivision between Wyman and Waltham, Quebec; power for this train is handled by road number 6538, the last CPR locomotive to wear the railroad's maroon and grey livery.
See also
- Portal:Trains/Anniversaries/May 29/More
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