The Bayfront Maryland Town Locals Hope Stays Off Tourists’ Radar

When I visit Maryland, I often find myself heading back to some of my favorite spots. After all, no one ever gets tired of exploring the rich cultural and dining scene of Baltimore or enjoying the old-school boardwalk charm of Ocean City. But the Old Line State is a unique place in that so much of its tourist scene is concentrated in a few locations, and its unusual formation makes many of its small towns incredibly well-kept secrets. That's the case for what's turning into my favorite hidden beach town in Maryland — Leonardtown, a small town of about 4,500 located on Breton Bay, around 88 miles south of Baltimore. This harbor town is the perfect destination for those who want an off-the-beaten-path getaway, where you can join the locals for a stay in a town that has everything you'd want — great food, fascinating historical sites, seasonal activities, and a bayfront view you'll never forget. The tourists haven't discovered this gem in force yet, which means it's the perfect time to discover its charms for yourself.

Why This Maryland Beach Town Flies Under the Radar

As one of Maryland's southernmost towns, Leonardtown is easy to miss. Few visitors to the state will come this far south, and most of the area is surrounded by water, so visiting will usually involve a long drive. That makes it one of Maryland's best-kept secrets, primarily thanks to the gorgeous view from Breton Bay. The beach here is peaceful with wonderful white sand, and is a popular, rarely crowded spot for water recreation.

Inland, the area is just as beautiful. This isn't a busy hiking area, but the nearby St. Mary's River State Park offers peaceful trails with beautiful waterfront views. The main trail, the St. Mary's Dam via Green Trail and St. Mary's Lake Loop Trail, is an easy 8.2-mile hike.

Best Things to Do in This Quiet Beach Town

Despite its small size, Leonardtown is rich in culture. There are several small farms in the area that transform into beautiful pumpkin patches during the fall. Leonardtown is also home to one of the best Italian restaurants in the state, Il Piccolo Morso, which is an ideal spot for a candlelight dinner to celebrate a couple's vacation.

If you're planning to stay for a few days in Leonardtown, you'll want a good home base. The Water's Edge Retreat is an amazing Airbnb in the area if you prefer more room to spread out and cook your own meals. The town has a rich history tied to the Underground Railroad, so make sure to visit the Old Jail Museum while you're in the area.

Have you visited this hidden beach town in Maryland before? If not, Leonardtown's summer season is when the town is at its peak, so tell a friend about this article and plan your escape to Breton Bay! If you're looking for some more unique stops along the way, check out Only in Your State's list of the best small towns in Maryland. And if this is your first time vacationing in the area and you want a little extra help planning activities, head over to Only in Your State's AI-powered travel planner and let it design a custom itinerary for your stay!