The Brass Donkey and the Freedom Trail in Boston

Not all the stops on the freedom trail are revolutionary. If you have ever walked to Old City Hall and saw a brass donkey outside its doors, you may have wondered, how did a brass donkey end up here?



Discover the stories of Boston along the Freedom Trail on our Solo smart phone navigated tour of the Freedom Trail, only on WalknTours app. You’ll see all the classic stops, plus learn the stories of Boston along the way. Tours are $5.99 each and roughly an hour long.

Now back to the story of the brass donkey. That old donkey was purchased on a trip to Florence by Roger Webb. He thought kids would love to see the donkey in Boston, so he shipped it back to Boston and donated it to the city. But the city of Boston didn’t have the same warm fuzzy feeling. It was decided that a brass donkey had no connection to Boston, or the freedom trail for that matter.


They told him to keep his donkey.


Roger was in a pickle. He has the big brass donkey and nothing to do with it. So being the quick thinker he was, he changed the script.


Roger said “au contraire mon frère, the brass donkey represents the Democratic party. And what better place than outside of the old city hall!”



The city finally caved and soon after this donkey was placed outside of Old City Hall.


But it did not take long for the Republicans to demand a brass elephant statue.


Just in front of the donkey you’ll find brass foot prints. Just next to them you’ll see an elephant and the words “Stand in Opposition”.





That’s all the city could muster up. Statues are expensive.


Locals say if you’re a democrat you should ride the donkey. And if you’re a republican you should stand in the footsteps with your hands on the donkey’s ears pushing in opposition.

To discover the stories of Boston and see the donkey up close for yourself, get the WalknTours app and take our tour “Freedom Trail Part 1 Revolutionary Boston!”. And don’t miss out on our popular tour of the Little Italy of Boston, the “Freedom Trail ‘The North End’ Part 2’.


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