"See You In September" by the Happenings always brings back memories of my summers as a kid, and the end of the school year.
Me too, and I'm sure lots of others.
Heaven is a Place on Earth by Belinda Carlisle: I flew out to Edmonton for a vacation in 1987 or 88. It was my first time doing a real trip through Alberta and the Rocky Mountains. At the airport, I rented a car. It was the first song that came on the radio. It was the first time I had heard it, but certainly not the only time on that trip. I think it was somehow bigger in western Canada than in Toronto. I associate it with Edmonton, driving past oil refineries, and seeing the mountains for the first time, driving west toward Jasper.
Juanita by Shania Twain: Associated in my mind with a long drive up Hwy. 144 from Sudbury to Timmins, obviously because the latter is Twain's home town, but also the strong contrast between the Mexican flavour of this song and the Northern Ontario wilderness.
California Dreaming by The Mamas and the Papas: Seems to be an anthem of the late 60s. As a kid I was too young to hit the road to California, but I could daydream a bit. The song has proven to be a classic.
Black Day in July by Gordon Lightfoot: Speaks of the same time frame, but certainly in a very different way.