Main Street Leonardtown is a genuinely thriving small-business town. From Fenwick Street Bookstore to Shepherd’s Old Field to the craft studios and local restaurants clustered around the Square, Leonardtown’s downtown is walkable, independently owned, and still growing — a rare thing for a small town this size. California, MD is the retail hub, anchored by centers like St. Mary’s Marketplace and Wildewood Shopping Center, where locally owned shops sit alongside newer additions like Tia’s Cantina and other independent restaurants opening up almost every year. Lexington Park, the gateway to NAS Patuxent River, has its own dense cluster of locally owned restaurants, coffee shops, antique and thrift stores, and neighborhood retail — and with nearly a quarter of the local workforce in STEM fields, it’s actually been ranked as having the highest share of high-tech jobs of any city its size in the country. Hollywood and the surrounding rural crossroads add family-run spots like The Cow & The Fish, while the Lexington Park Business Association and the St. Mary’s County Chamber of Commerce actively work to support and grow these independent businesses countywide. It’s a reminder that the county’s small-business spirit isn’t a downtown-only phenomenon — it shows up in strip centers, crossroads towns, and neighborhood corners throughout St. Mary’s.