379Q: Obscure 1970s-80s YA: Boy’s strange adventures, betrothed/young married kids (maybe cousins/gypsies), family secrets, reunion at Kentucky Derby with girl in polka dot dress & ‘My Old Kentucky Home’ playing

This has bugged me for years—posted about it on Library Thing back in 2018 (link: https://www.librarything.com/topic/292966#6515048) with no solves, but adding more details now in case it clicks for someone.

I read this book in England in the late 1970s/early 1980s (probably on a shared bookshelf at my dad’s work—likely a US import or British edition). It was a quirky/strange YA (young adult) book, from a boy’s perspective, more mystery/adventure with family secrets than straight romance (though maybe light romantic elements or betrothal tension).

Key bits I remember:

  • Two children (boy protagonist + girl) who were either betrothed young, arranged to marry early, or possibly cousins (that part’s fuzzy/weak).
  • Strange adventures happen to them.
  • Possible gypsy/Romani/traveler family background (one or both sides—maybe adding outsider secrets, wandering, or cultural quirks).
  • The story builds to a climax/reunion near the end: They find each other again at the Kentucky Derby (or a Derby-related event). He spots her in the crowd (possibly amid race horns or excitement), she’s wearing a polka dot dress, and “My Old Kentucky Home” is playing (or tied to the scene somehow).
  • Not primarily a romance; more YA adventure/mystery with a poignant, symbolic ending.

No idea on title/author/cover—it’s obscure, maybe small-press or regional. Anything ring a bell? Even partial matches or similar books would help!

Thanks in advance—it’s one of those that pops into my head every few years.

3 thoughts on “379Q: Obscure 1970s-80s YA: Boy’s strange adventures, betrothed/young married kids (maybe cousins/gypsies), family secrets, reunion at Kentucky Derby with girl in polka dot dress & ‘My Old Kentucky Home’ playing

  1. Gill

    If they were horse based/background, then the C W Anderson books may be worth checking. It’s the right(ish) time frame if reprints are taken into account.

    They were horsey, for chiidren, and there’s at least one of them mentioning ‘My Old Kentucky Home’ (the title ‘Another Man o’War’, but otherwise not a match to your description). Another title is ‘Blaze and the Gypsies’, for which I have no further info.

    It seems at least some of the books may be illustrated with pencil sketches.

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  2. Marisa

    Not sure if the inquiry came from the same source, but user Kathy_Moon on LibraryThing’s “Name That Book” group has suggested Ellen Raskin’s “The Mysterious Disappearance of Leon (I Mean Noel)”. Which I know I read at some point in late childhood, but I remember so little about it that I wouldn’t have come up with it as a suggestion myself.

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  3. Mama Squirrel

    What about Ellen Raskin’s The Mysterious Disappearance of Leon (I Mean Noel)? The arranged marriage fits, also there is a subplot about racehorses.

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