President Harry Bentley’s Guide to Boston, 1940

Mr. Bentley liked to be accommodating to out of town visitors and guide them to all the best places in Boston – including letting them know where to rent a tuxedo. From sightseeing trips to the best restaurants to Red Sox games and horse races, he proudly displayed all that Boston has to offer.

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“Get your Bearings”


“These narrow, winding street were not laid out by a planning board. They follow lines of travel established by the early settlers, who made their roads and by-paths to meet their convenience.”

Parking and Traffic Rules

“Use caution and you will have little occasion to use your horn. A horn-tooter is a pest.”

sports and places to eat

Beaches and boat trips

sightseeing trips

10 sightseeing trips that go out as far as Plymouth and the Cape.


Tuxedos, Train stations, and The Bentley School


“No one can tell whether a man is wearing a rented outfit or one that is his own.”




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