Annapolis Roads Centennial Celebration

Founded in 1926, Annapolis Roads was the vision of a pioneering woman who assembled nationally recognized landscape architects and golf course designers to create one of the Chesapeake Bay’s premier residential communities. During the Roaring Twenties, it became a favorite destination for visitors and socialites from Baltimore, Washington, and Annapolis.

One hundred years later – 2026 –  we’re excited to celebrate that history, reconnect with neighbors old and new, and maybe even bring a little of the Roaring Twenties back to Annapolis Roads as we celebrate our Centennial together.

ARPOA is planning a Centennial Celebration that will include an afternoon family event at The Overlook on Saturday, September 26, 2026. If there is sufficient volunteer support, an evening reception for adults will also be planned (date to be determined).

Whether you’ve lived here for decades or just moved into the neighborhood, we invite every resident to help shape our Centennial celebration.

This 100th-year celebration marks a milestone in our journey, honoring the past while looking forward to a bright future. Join us in celebrating the stories and people who have made Annapolis Roads a cherished place to live.