| ATCHISON | Judy Garland sang the Oscar-winner On The ... Topeka And The Santa Fe |
| SANTAFE | Judy Garland sang the Oscar-winner On The Atchison Topeka And The ... (5,2) |
| TOPEKA | "Do you hear that whistle down the line?" asked Judy Garland. "She's the only one that'll sound that way; On the Atchison, ... and the Santa Fe" |
| MEETME | Judy Garland sang The Trolley Song in ... In St Louis (4,2) |
| MIGHT | In State Fair, Dick Haymes sang the Oscar-winning song, It ... As Well Be Spring |
| REGINAKING | "If Beale Street Could Talk" Oscar winner on the list |
| WATERFRONT | Multiple Oscar winner On the ___ |
| EMPORIA | City between Topeka and Wichita |
| EMBRACEABLE | Judy Garland sang, "Just one look at you, my heart grew tipsy in me; You and you alone bring out the gypsy in me" in the Gershwin song ... You |
| LEMON | Judy Garland sang, "Where troubles melt like ... drops; Away above the chimney pots; That's where yo |
| EYESOF | Judy Garland sang, "Come with the love light gleaming; In your dear ... blue; Meet me in Dreamland; |
| HEPBURN | Katharine, the Oscar-winning actress, was no relation of the Oscar-winner Audrey (7) |
| NINA | What ship, with the Pinta and the Santa Maria, did Christopher Columbus command on his first voyage to the New World in 1492? (4) |
| MADEME | Judy Garland sang, "I must tell you what I'm feeling; The very mention of your name sends my heart r |
| FTDODGE | Old Army base on the Santa Fe Trail, briefly |
| INDEPENDENCE | City in Missouri which was starting point for the Santa Fe, Oregon and California Trails (12) |
| PINTA | The Nina, the ___, and the Santa Maria |
| GLAD | Judy Garland sang, "You made me happy, sometimes; You made me ...; But there were times, sir, you ma |
| INST | Judy Garland sang Meet Me ... Louis (2,2) |
| HOIST | A Santa cheer can be a winner on the crane (5) |
