Leonardtown in St. Mary’s County has advanced as one of 40 national finalists in Parade Magazine’s America’s Favorite Small Towns competition for 2026. The announcement came after months of public voting that drew hundreds of thousands of ballots nationwide.
The competition presented by Parade and Steller honors communities with populations under 250,000 that showcase charm, history, culture, natural beauty and neighborly spirit. It aligns with celebrations leading to America’s 250th anniversary. Community voting opened November 17 2025 and closed before national finalists were revealed March 1 2026.
Leonardtown earned its spot through strong local support and community efforts to highlight the town’s historic charm waterfront views and close-knit atmosphere. Town officials expressed gratitude to voters in a March 3 2026 announcement. “We’re thrilled to share that Leonardtown has officially been named a finalist in Parade’s America’s Favorite Small Towns competition. This is an incredible achievement and a true testament to the pride, passion, and community spirit that make our Town so special.” As a finalist Leonardtown will appear in a special print issue of Parade Magazine titled “Favorite Small Towns in America” distributed nationwide at the end of May.
The 40 finalists represent diverse regions from coastal areas to mountain towns and vibrant main streets. Examples include Lodi California Lancaster Pennsylvania Fredericksburg Texas Kalamazoo Michigan and Dunedin Florida. Leonardtown joins this group as a Southern Maryland representative. The complete list of finalists is available at https://americasfavoritesmalltowns.parade.com/.
Next steps include judging to select regional winners announced June 1 2026 followed by the national winner revealed June 12 2026. The winning town will host a Parade x Steller celebration during its July 4th festivities and receive additional national exposure. A trip giveaway tied to the competition has its winner announcement forthcoming.
Leonardtown’s push began earlier with calls for votes in January 2026 emphasizing its role as a historic county seat in Southern Maryland. The town known for events like oyster roasts parish potlucks and Friday night parades drew on resident enthusiasm to build momentum. This finalist status builds on prior recognitions such as topping a Maryland culture vote in 2025 for its small-town traditions.
Southern Maryland benefits from such national spotlights as they draw attention to the region’s maritime heritage historic sites and community events. Leonardtown’s advancement underscores local pride and could boost tourism interest in St. Mary’s County amid ongoing efforts to promote the area’s waterfront and cultural assets. Residents and supporters continue to celebrate the milestone crediting collective voting and passion for the town’s exceptional character.