Fall is a special time in Leonardtown. The vibrant Fall colors on display around the Town are truly breathtaking. Take in the tranquil surroundings as you stroll along the brick paved sidewalks or gather with friends and family in the beautiful Town spaces. There are many unique hidden treasures to be found - both historical and intriguing. The Town truly comes alive  - the businesses decorate for the Annual Scarecrow Stroll and the holiday event season kicks off with First Friday in October (Friday, October 7, 2022). We invite you to come see and explore the beautiful sights and sounds of Leonardtown in the Fall and to vote for your favorite Leonardtown Scarecrow. Plan your visit with our checklist below. If you're a business, please consider exploring your creativity and making an entry (if your business is off the Square, we'd be happy to find a location for you). For more information, please contact Jennifer Stotler at: leonardtownmaryland@gmail.com, 301-247-7611 or use this link to register www.flowcode.com/page/leonardtown.