
UPDATE: I’ve added a Spotify playlist at the bottom of the page featuring these songs & a few extras from the summer of 1966.
I wanted to make a quick point that when people compile list of great summer hits, at least 3 come from 1966.
Among them is Billy Stewart’s blistering, hyper version of Gershwin’s “Summertime.” The idea to do this wild, fast arrangement of this, usually, slow song came to him in a dream. He played it on a piano & performed to vocalese parts for the session men. After that, they then recorded it in one take.
The Loving Spoonful gave us probably one of the all-time great summer hits, “Summer In the City.” Before ‘Summer In the City’, they had another hit with a summertime vibe, ‘Daydream’.

The Kinks “Sunny Afternoon” is another hit from the summer of 1966 & in typical later Kinks fashion, it mixes social satire into a summer song. Ray Davies sings the song from the point of view of a rich, Preppy douche bag, complaining that he may have to sell his yacht to pay his taxes & his girlfriend left him because he abused her. By the end of the song, he is going to just hook up with a ‘big, fat mama’ and continue ‘living a life of luxury’ ‘in the summertime.’

Although not exactly a summer song, “Sunshine Superman” by Donovan has always been placed on the list of summer songs. This song helped Donovan escape the “next Dylan” tag and kicked off his psychedelic minstrel phase of his career. The guitarist on this track is future Led Zeppelin guitarist Jimmy Page.
Bobby Hebb’s “Sunny” is also frequently listed as a summer song & it was a hit in the summer of 1966, but it was originally a tribute to his late brother, whose name was Sonny. The record company thought it would sell better as “Sunny.”

It actually came along after the summer was over, one that has to be included is by Old Blue Eyes himself, Frank Sinatra. “Summer Wind” was more of a hit on the new radio format called Adult Contemporary or Easy Listening. Sinatra & his pal, Dean Martin, had a resurgence in the mid-60s. Their music became popular again in the 90s with hipsters. “Summer Wind” was even featured in an episode of The Simpsons where Martin sang it.
I was going to say that the least remembered of the summer hits from that year is “Happy Summer Days” by Ronnie Dove. While it hasn’t turned up on any major list or CD compilations of summer hits over the years, I found out on his Wikipedia page that Amazon used it in a commercial campaign called ‘Summer Delivered’ in 2019. Dove was not a major star, but got a lot of airplay while being on a small label. His style is kind of a pop country that sounded dated even in 1966. In my novel Mykel makes fun of Alice for liking Ronnie Dove.
Other songs that are summer songs from that year (these include the word ‘summer’ in the lyrics): ‘Red Rubber Ball’ & “Turn Down Day” by the Cyrkle, “Bus Stop” by the Hollies, “Green Grass” by Gary Lewis & the Playboys, & ‘See You In September’ by the Happenings.
I will also mention the song, ‘I Lost My Heart at the Fairgrounds’ by Glenda Collins, because most fairs take place in the summer.