GM was tipped off to this above video featuring 1960s singer-songwriter Ricky Nelson performing “Everybody’s Talkin'”. He starts out walking up Wisconsin Ave. then it cuts to what appears to be a live recording of him playing along the rapids of Great Falls.
The YouTube clip identified the video to have come from “the late Sixties”. The song was written in 1966. And one of the stores you can see him walk past is the old Britches (which is now the Ralph Lauren). Britches opened in 1967, so it’s at least from as late as that. The bus is a DC Transit bus, which ran from the end of streetcars until it was absorbed by WMATA in 1973.
You can compare how the store fronts have changed:
The parking lot sat where the Apple Store is now. So the first red brick building is what’s now Madewell, and so on.
It’s also a good reminder of how much the store fronts have changed over the years despite the supposedly rigid preservation. They’ve become a fancier version than they were at the time Congress decided to preserve them.
Oh, and note how the sidewalks were concrete. Brick sidewalks are another bit of anachronism masquerading as historical.
The Georgetown Metropolitan 
Great shot of Wisconsin in the 1960s! I had forgotten about the concrete sidewalks. When were they changed?
Rick Nelson performed at the Cellar Door in Georgetown in 1968, and this was probably filmed when he was in town for a week. The legendary nightclub was on a early rock and roll revival kick. One week it was Bill Haley and the Comets, the next week Rick Nelson, then The Platters, then Bobby Darin. Little Stevie Wonder made his comeback at the Cellar Door (he was a pop singer as a kid).
When I entered the Coast Guard in 1966, my college girlfriend broke up with me.
When I was transferred to Washington, DC, three years after Boot Camp, she would invite herself to visit me for a weekend. I was living in a furnished apartment provided by the Coast Guard. She said, “With these white walls and blonde Danish furniture, this seems like the vanilla apartment you’d pick.”
I took my former girlfriend to a popular night club called the Cellar Door to see the Chad Mitchell Trio. We were seated at a table touching the stage. An announcer came out at curtain time to announce that the Chad Mitchell Trio were unable to perform. Rick Nelson had “kindly consented to take their place.” I was excited to be sitting three feet from him while he said hello to Mary Lou. When Rick Nelson came out he reached down to shake hands with the six of us sitting at the stage margin. Because Rick Nelson’s career took a hit after the British Invasion, back in the cab, Girlfriend 6 scoffed, “I can’t believe you took me to see Ricky Nelson !!!”
I naively envisioned a romantic interlude with an old girlfriend. Instead, when we returned to my “vanilla apartment,” I offered her my “blond Danish” bed and slept on the couch. For the rest of the weekend, I masked any remaining physical attraction.