The long-running hill-climb is widely regarded as one of the best in the country, and attracts a large number of spectators every year.
Brailsford used to live in Sheffield, only a short distance from Monsal Head, and rode to the event in full Team Sky kit.
He then mixed with fans and even posed for a photo taken by Rob Copeland with pint in hand. It was a far cry from the pressured environment of watching his team during the biggest races on the calendar.
"The secret's out," said Copeland on Twitter. "Chris Froome's recovery drink from the horse's mouth. Amazing to see Sir Dave."
Brailsford also stopped to talk to YouTuber Cameron Jeffers of CyclingCam, who posted his mini-interview with Brailsford online.
Jeffers asked Brailsford whether he was tempted to take part himself.
"I'd love to really, but I think I'll have the same excuse as one I heard a minute ago, which was 'I couldn't race because the dog was sick". That's when you know you're at a local club event, it's nice to hear!"
With no Team Sky riders taking part in the Monsal Hill Climb this year, perhaps Brailsford was indulging in a bit of talent spotting for the future.
Adam Kenway (Raleigh-GAC) took the men's honours, with Rebecca Goodson (Velo Schils Interbike) securing the women's title.
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