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In Avengers: Infinity War, when Spider-Man is clinging to the outside of The Maw's ship as it's leaving Earth, Iron Man provides Spider-Man with a new suit.

Just as Spider-Man exclaims how cool the new suit is, Tony has F.R.I.D.A.Y. deploy a parachute that's a part of Spider-Man's suit, to get Peter back to Earth. Well, right after Tony commands F.R.I.D.A.Y. to deploy the chute, and Peter gets sucked away, Tony yells to Peter:

"Happy trails, kid!"

To me, this seems like it might be a reference to something, and I'm thinking a movie, since one of the recurring elements between Peter and Tony in this film is making movie references. But, I've tried searching for the reference and have been unsuccessful so far.

So, is this line a movie reference? If so, which?

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It's a TV (and old radio show) reference. Both Die Hard and Avengers are referring to a song. It's a pop-culture way of saying, "Goodbye!"

When Tony Says it to Peter, he's implying, "Happy Trails, until we meet again!" in a friendly way.

When Bruce Willis says it to the bad guy, it's a sarcastic way of saying "Goodbye." The Roy Rogers reference also ties in with John McClane's cowboy persona from the rest of the movie.

Happy Trails by Dale Evans, was the theme song for the 1940s and 1950s radio program and the 1950s television show starring Roy Rogers and Dale Evans Rogers. It was always sung over the end credits of those programs.

The Roy Rogers show was a cultural icon and in reruns well into the 1960s.

Lyrics:

Some trails are happy ones

Others are blue

It's the way you ride the trail that counts

Here's a happy one for you

Happy trails to you,

Until we meet again

Happy trails to you, keep smilin' until then

Who cares about the clouds when we're together?

Just sing a song and bring the sunny weather

Happy trails to you, 'till we meet again

(I guess I'm the old guy here.)

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    The Roy Rogers show was a cultural icon and in reruns well into the 1960s. Die Hard was made in 1988, which is closer in time to Roy Rogers than it is to today! RDJ is older than me, his character would know the reference though too young to have watched the original show. Bruce Willis probably/likely watched the Roy Rogers show as a kid.
    – Rocky
    May 10, 2018 at 1:03
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    IMO, Tony wasn't referencing the old western TV show or radio program that was around 20 years before he was even born. It's much more likely that he was referring to a movie, with that movie being Die Hard (again, since movie references are a reoccurring theme between the two of them, and not just TV shows/media/etc.). The fact that in Die Hard it's a reference to that western program is specific to Gruber and his interests. So, really, Tony was referencing a scene that contained a reference, and not referencing the same as John was.
    – Charles
    May 10, 2018 at 2:41
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    Geez. I thought everyone knew this. +1 @Charles It's a cultural icon that became one because of the original radio and TV shows. Sure, it's not trying to parody those things, but it's obviously a call back to them and the cultural icon they created. That's how it came to be a common farewell. And in particular, when used seriously, it's a wish of good tidings and well being, things Tony would obviously want for Peter.
    – jpmc26
    May 10, 2018 at 3:45
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    jpmc is correct here. There’s just no way Tony Stark is referencing a Die Hard movie in Avengers. It would be like saying “May the force be with you” is from Family Guy. “Happy Trails” is the definitive closing song from Roy Rogers. Ask your parents or grandparents. This one is a no-brainer.
    – Rocky
    May 10, 2018 at 5:31
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    It's also possible he's not really referencing anything here. As some one who had heard the phrase "Happy trails" but wasn't aware of it's origins, it's just an idiomatic phrase for "goodbye" or "see you later". "Making a reference" to something comes with the implication that they are aware of the origin of the phrase, which Tony may not have been.
    – Shufflepants
    May 10, 2018 at 15:44
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Was this also a movie reference?

Quite possibly!

When performing a Google search using "happy trails movie", in the Images results, one of the thumbnails was of Alan Rickman in Die Hard.

From the end of that film, Bruce Willis's character (John) says the following to Rickman's character (Hans), just before Rickman goes flying out a window:

"Happy trails, Hans"

The similarity between the two scenes is that Tony sends Peter back to the Earth's ground, just as John did to Hans (though, with a different context and method).

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    The "Happy trails" line in Die Hard was a reference to Westerns, because Gruber was calling McClane a cowboy (John Wayne -> Gary Cooper). And when McClane shoots Gruber I don't think he intended for him to fall out the window. - It would seem rather odd to reference a character who falls to his death. I'm sure Tony wouldn't want that fate for Peter ;-)
    – Oliver_C
    May 9, 2018 at 19:33
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    Good find! I can totally see Tony making this reference, sarcastically of course.
    – Steve-O
    May 9, 2018 at 19:35
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    Both Die Hard and Avengers are referring to the same song from an old TV show . . . see my answer for details.
    – Rocky
    May 9, 2018 at 22:13
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    Given the common detail in the two scenes - IW and Die Hard's - I would say that while Die Hard does refer to Roy Rogers, IW refers specifically to Die Hard. Unless Roy Rogers fell from great heights a lot. It is also one more "ancient movie" exchange between Stark and Spiderman.
    – deg
    Aug 3, 2018 at 9:36
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This was a very popular old song. Anyone Tony Starks age would have had his parents singing, quoting, and even listening to it in their new-fangled CD player.

or

The song is well known, but not really by a younger crowd. Stark seems to say it as another joke about Spider Man's age. Though it could be there just to contrast the age difference. At 35 I know the song and know it's old. At 18 I wouldn't have ever heard of it.

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    I suppose it could also be a reference to "Charles Lloyd & The Marvels with Bill Frisell" They usually do (sometimes do IDK) Happy trails as an encore "after the show is over" It's an odd reference but the writers have been known to stretch a bit.
    – coteyr
    May 10, 2018 at 16:46

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