Democratic Donkey and Republican Footprints

Boston, Massachusetts
The Democratic Donkey and Republican Footprints are unique monuments that can be found right outside Old City Hall in Boston, Massachusetts.
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About This Location

Nestled along Boston’s Freedom Trail, just outside the iconic Old City Hall, stands a peculiar yet endearing sight: a bronze donkey statue attracting the curiosity of children and adults alike. Beside it lies a set of cast footprints adorned with the motto “Stand In Opposition,” offering a silent yet poignant counterpoint.

This whimsical addition to Boston’s landscape is the brainchild of Roger Webb, a passionate preservationist whose journey began in Florence, Italy. There, amidst the artistic splendor of a local shop, Webb encountered a life-sized bronze donkey statue that captured his imagination. Convinced of its potential to delight and engage, he resolved to bring it back to Boston, envisioning it as a playful distraction along the historic Freedom Trail.

However, Webb’s initial enthusiasm was met with skepticism by city officials, who questioned the relevance of an Italian donkey statue on Boston’s revered trail. Undeterred, Webb persevered, proposing a symbolic connection between the donkey and Boston’s long-standing affiliation with the Democratic Party, which had governed the city for over a century.

Yet, as the donkey found its rightful place in the courtyard of Old City Hall, Republicans voiced their dissent, demanding representation for their party as well. Webb, ever resourceful, commissioned his cousin to craft a set of footprints adorned with tiny elephant drawings, providing a platform for those who stood in opposition to the Democratic symbol.

Despite initial doubts, Webb’s creation quickly endeared itself to the community, becoming a beloved fixture along the Freedom Trail. Children clambered atop the donkey, while parents and grandparents delighted in its whimsical charm, a testament to Webb’s vision and perseverance.

Today, the donkey stands as a cherished landmark, a testament to the power of imagination and the enduring legacy of one man’s passion for preservation. As visitors stroll along the Freedom Trail, they pause to admire this charming statue, a whimsical reminder of Boston’s rich history and vibrant spirit. And for Roger Webb, the love for his beloved donkey only continues to grow, a fitting tribute to a journey fueled by creativity and dedication.


Address: 45 School Street, Boston, Massachusetts
Place GPS Coordinates: 42.357861, -71.059528
Parking GPS Coordinates: 42.357861, -71.059528
Parking Notes: Street parking is available nearby along with garages and lots.

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