I found this great quote by Ruth Gordon (aka Maude in Harold and Maude) describing the time, during Prohibition, when the expression “doing the town” meant something. I can't describe how much I love identifying with a person or a time years, decades, or centuries later. She said the following is a typical itinerary for dinner to dawn in the 1920s:
"For a really swell night out in the Twenties you’d probably start out at an elegant place like the Crystal Room in the old Ritz-Carlton on Madison Avenue. Oh, did they have wonderful food there. You ordered a la carte of course. Anything you wanted. You’d start off with the oysters, then you’d have a lovely soup with croutons on the side. Then, if you were truly eleganza you’d have some fish, and then you’d have the game, if it was in season. (That was Fanny Brice’s great restaurant line—“Give me anything, as long as it’s out of season.”) Or you’d have the gigot—which was a big thing all by itself. Nobody thought too much about salad. Salad, in those days, was Lobster Salad or Chicken Salad. And the desserts were paradise—Baked Alaska and profiteroles! Nobody cared about diets. Everybody ate chocolates and cakes and whipped cream. Adele Astaire [sister of Fred], a friend of mine, had a chocolate soda every day of her life, as I did for the most part, and once I said to her, “Why don’t we ever get fat?” She said, “We are just fortunate that we are blessed with poor assimilation.” I don’t know what she meant by that, but it’s true that we ate anything that we wanted to and we certainly did not get fat.
After a lovely late dinner at the Crystal Room you’d go over to Harry Richmond’s Wigwam Club. Of course it was during Prohibition so you’d have to order something like Chicken à la King just to hold the table, but actually you were there just to have more illegal drinks. Depending on how you felt at two or three in the morning, you’d make your way up to Harlem and go to Small’s Paradise or The Savoy to hear the great bands. Then you might have a snack at one of the little Harlem bistros where you would eat what we now identify as “soul food.” At seven or eight in the morning you’d arrive at Reuben’s, which was on Fifty-eighth Street between Fifth and Madison, where you would have breakfast. And everybody who was anybody was always there.
Going out in the Twenties was so glamorous, so dazzling. Everybody was beautiful and everybody was sexy and nobody was economical. If you weren’t glamorous and beautiful you stayed home. But the whole idea was to have money, to be striking. Nobody was concerned about being cultured or being talented."