Written and first recorded by Ruthann Friedman (1967).
Hit version by The Association (US #1 1967).
From the wiki: “‘Windy’ was written by Ruthann Friedman, a transplanted New Yorker who moved to Venice, California, where she hung out with the cream of L.A. Pop royalty – a 16-year-old sneaking into the Troubadour in the early ’60s and, then, an 18-year old starting to write and play her songs on the guitar, making friends with David Crosby, Van Dyke Parks, and Tandyn Almer, author of ‘Along Comes Mary’, another big hit for The Association. (It would be Parks who would introduce Friedman to The Association.)
“Friedman later recalled ‘I just was bopping around playing music with my friends, going to San Francisco, staying with friends up there, staying down here in Los Angeles. It was kind of a gypsy life that a lot of us led. Honestly, I just felt this is what I expected to happen. It’s what I anticipated would happen.’ Friedman remembers writing ‘Windy’ in about 20 minutes while living in an apartment in Crosby’s house. ‘People said it was about my hippie boyfriend up in San Francisco. I never had a hippie boyfriend. These days, looking back at myself in my mid to late 20s, I finally realized I was talking about me in that song, and how I wanted to be.'”
The Association, “Windy” (1967):