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I'd say Blackfriars > Elephant & Castle > Camberwell (via Walworth Rd) & continue straight up Denmark Hill to Herne Hill is a pretty straightforward bet.
Maybe not the chillest route (not sure how Elephant & Castle's roundabout replacement is these days), but definitely the most straightforward. And least likely to end up with wrong turns.
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What @mmccarthy said, though Walworth Road is not really very chill! And Denmark Hill depends on your appetite for hills.
From Elephant, I'd probably go past Kennington (massive cycle lane), up towards Brixton and turn left at Brixton Jamm up Loughborough Road > Milkwood Road.
Slightly less direct, but more chill. -
E&C roundabout is 1. not a roundabout anymore and 2. is totally fine if you're not a complete moron. @mmccarthy 's suggestion is what I would do/did when I worked at Blackfriars and commuted to Crystal Palace.
Alternative is E&C - Kenington - Oval - Brixton Rd - Loughborough Road - Loughborough Junction - Milkwood Road
Less of a high streety vibe than Walworth Rd. But if you go Walworth Road you get to stop at Bagel King.
whats the chillest route between temple/holburn and herne hill in the late evening?
im not too familiar with south of the river, havent done much exploring yet, and would prefer not to wrong turn myself into a bad spot when im knackered.