Over three decades in business, Gavin has built partnerships with other business owners and community groups to initiate a number of successful, recurring events, including, “Dining Under the Stars,” the “Annapolis Fringe Festival,” and “First Sunday Arts Festival.” These efforts led to a gradual revitalization of West Street, now known as the Annapolis Arts District -- a thriving hub for new businesses, arts, and community events.

Gavin’s two terms as Mayor were defined by innovation and results. He introduced governance reform, diversified leadership, and implemented community-driven planning to address long-neglected issues such as flooding; revitalization of the downtown economy; a more sustainable approach to transit; and greater representation and inclusion for marginalized and underserved communities.

The results include budget management reforms that led to the highest bond ratings ever achieved by the City of Annapolis; community participation in critical decisions including a vibrant, community-built concept plan for a re-imagined, flood-proof City Dock; new parks and trail connections; a range of new, sustainable electric transit services; a new downtown parking garage built through an innovative P3 partnership; a transformation plan for public housing; a more transparent development process; and new programs and resources to combat substance abuse and gun violence and create opportunities for at-risk youth.

Gavin’s terms as Mayor were also marked by unprecedented challenges including the tragic mass shooting at the Capital Gazette, the Covid-19 pandemic, and a series of natural disasters, including a tornado and increasingly frequent flooding events. Throughout these challenges, he worked with the county, the state, and federal partners to source funding and secure services to bring relief to impacted residents and businesses.