A medieval toll dodge means Freemen can still drive sheep across a bridge

September marks the return of one of London’s quirkiest rituals.

A herd of sheep will be driven across Southwark Bridge on Sunday 27th September 2026 in honour of an ancient London ritual. It’s part of the Woolmen’s Sheep Drive, an annual event that’s been running for well over a decade but has its roots in something much older, and raises money for the Woolmen Charity and the Lord Mayor’s Appeal.

The sheep will be driven by a variety of Freemen of the City and a special celebrity guest whose name is yet to be announced. Previous celebs that have had a crack at driving the sheep include Mary Berry, Alan Titchmarsh and Michael Portillo.

So, Like, Why?

Well, it has to do with a very old agreement between the Freemen of the City and the folks that used to toll London Bridge. It was an understanding that dictated the woolmen’s ‘right’ to drive sheep over the bridge to get them to Smithfield’s Market.

This all happened so long ago that no one’s quite sure how long the tradition has been going. A fair guess would be that the rights were originally given in the mediaeval age.

Nor is it clear when the last drive was before the practice was shut down. The experts think it was probably since the rise of motor vehicles and we’re inclined to agree with them – they are the experts after all.

Can We Go and Watch?

Yes, indeed you can, though the crossing itself is a ticketed affair. Access to actually walk the bridge with the sheep is restricted to registered Freemen of the City and their guests, with livery companies and teams booking timed slots across the day, but spectators are welcome to line the bridge and watch for free as each group makes its crossing.

Everyone’s invited to the Livery & Wool Fair at the north end of Southwark Bridge, which runs alongside the drive. Expect stalls from livery and wool-trade businesses, rare-breed sheep on show, expert blade-shearing demonstrations, and food and drink stands. Lamb burger anyone?