The Eliot Lounge was a great bar which later turned into a great sports bar. I enjoyed a few drinks there myself. This article, written on the closing of the Eliot Lounge, captures the essence and spirit of the bar.
Check out those prices! Madeline has this dated March 15, 1949.
I believe this would have been on each little table at the Kenmore Hotel bar. Notice the tab on the right hand side. There is a slot on the left side where that goes into so she stands up. This is Beverly Stull, who played at the Kenmore from time to time. All I came up with in my research on Beverly is this one sentence in a gossip column in the Pittsburgh Post Gazzette on May 1, 1947: "Beverly Stull, the Leechburg accordionist, home for a few days after a string of winter engagements in California, pulls out over the weekend again for a booking at the Kenmore Hotel in Boston."
Hard to see, but this is a swizzle stick from the Kenmore hotel bar. For more info on the Kenmore hotel, see a previous post here.
Madeline must have carried big purses to put all these goodies in! Here is the drink menu of rum drinks:
60 cents for a frozen daiquiri!!
History of radio station WJZZ which broadcast from the Pink Elephant is here.
Front and back of matchbooks.
Here is a menu from the Stueben restaurant and New Vienna Room.