It was named after the neighbouring heritage site of the only lasting (and working) windmill (aka Ashby's Mill) in the London area.

It went through various phases of being a bar that attracted locals, bikers, and the Irish community; by the end of the 1990s, it was hosting DJs, poets and the occasional live bands.

Early gigs included a semi-secret double bill of Calexico and Kurt Wagner (of Lambchop) followed by a gig by The 5.6.7.8's, just after they had appeared as the house band in Quentin Tarantino's Kill Bill: Volume 2.

[6] Bands to have played gigs at The Windmill include: …And You Will Know Us By The Trail Of Dead,[5] Bloc Party,[3] Caitlin Rose,[5] The Crimea,[3] Damo Suzuki,[7] Guillemots,[3] Hot Chip,[1] Los Campesinos,[3] Scritti Politti,[5] Sorry,[8] Stereolab,[5] and The Vaccines.

[5][6] In recent years, the venue has been connected with a resurgence of the South London guitar rock scene, due to frequent shows there by bands such as Black Country, New Road, Squid, the Fat White Family, and Black Midi, the latter being a resident act from 2018 onwards.