Leroy Anderson wrote the music for this song during a heatwave in July of 1946, while staying at a cottage in Woodbury, Connecticut, with his wife and 18-month-old daughter. Anderson was an orchestral composer who lived in the Boston area and moved to Woodbury permanently in 1948, where he lived until his 1975 death at age 66. He had a big hit in 1952 with the song "Blue Tango."

Arthur Fiedler premiered the song with the Boston Pops, who Leroy was an arranger for earlier in his career. Words for "Sleigh Ride" were added in 1950 by Mitchell Parish, and the song has since become a Christmas classic.
Like "Winter Wonderland," this song does not make any specific reference to Christmas, but the seasonal imagery has made it very much associated with the holiday. It's hard to think of a sleigh in winter without thinking of Santa.

The lyrics, "Like a picture print by Currier and Ives" refer to a printmaking firm that produced some of the most iconic and popular American artwork of the 19th century. The company specialized in publishing hand-colored lithographs that were sold inexpensively to the American middle class.

The Ventures did an instrumental version that is based on their hit "Walk - Don't Run." Another unusual take on the song comes courtesy of The Ronettes, who recorded it under the direction of producer Phil Spector. This version has the famous "Ring-a-ling-a-ling Ding-dong-ding" backup vocals, and has become one of the more popular recordings of the song. It was included on the 1963 album A Christmas Gift for You from Phil Spector, which had the misfortune of being released the same day US president John F. Kennedy was assassinated: November 22, 1963.
Other artists to record this song include Neil Diamond, Ella Fitzgerald, Amy Grant, Harry Connick, Jr., Herb Alpert, the Spice Girls, TLC, Kenny G, KT Tunstall, Air Supply, the Carpenters, the Mormon Tabernacle Choir, The Hampton String Quartet, Hilary Duff, Squirrel Nut Zippers, Vera Lynn, Natalie Cole, and She & Him, and fun. A version by Bela Fleck got a Grammy nomination in 2009 for Best Country Instrumental Performance.

According to ASCAP, this was the most-played holiday song on American radio from 2009-2012, beating out "Winter Wonderland," "The Christmas Song" and "Let It Snow! Let It Snow! Let It Snow!."
Anderson wasn't the only composer to write a wintry tune in the midst of a heatwave. Mel Torme and Bob Wells penned the perennial favorite "The Christmas Song" to cool off during a stifling summer in 1945.

For Anderson, the temperature wasn't even a consideration. "A composer seldom gets ideas for music from his environment," he explained in a letter to Icelandic Radio (as quoted by the Leroy Anderson Foundation). "Ideas come from inside his head and it makes little difference where his body happens to be. All a composer needs is solitude and quiet so that he can think without being interrupted or distracted. For this reason some of my ideas have come at very illogical times. Many people think that I wrote 'Sleigh Ride' in the Winter after seeing a sleigh go past my house. As a matter of fact 'Sleigh Ride' was written, not only in the summer, but in the midst of the biggest heatwave of the year."

The Ronettes recording has become the most popular. Since 2018, it has been a regular visitor to the UK and US singles charts during the festive period.