24 Hours in St. Mary's

While there are more than 24 hours worth of things to do and see in St. Mary's, you can still pack loads of fun into just one day. We’ve put together an itinerary to give you an idea of what you can do with 24 hours in St. Mary’s. Feel free to skip, add, or rearrange activities – it’s your day to enjoy and explore!

Pro tip: Check out our Events Calendar to see if there’s anything special going on the day of your trip and adjust your itinerary accordingly!

Day One Morning

Begin the day with a stop at St. Inie’s Coffee. Awaken your senses with a cup of freshly brewed pour-over coffee and sweet beignets, and take a moment to peruse the shelves of new and used books. There’s nothing wrong with getting a souvenir in the first place you stop!

Once you’re feeling energized, drive about 10 minutes south to Historic St. Mary’s City to walk the historic grounds, see the magnificent Maryland Dove, and even watch archaeologists at work.

Day One Afternoon

Hop in the car and head just a few minutes south to culinary hotspot Ridge and enjoy a waterfront lunch at Pier450, SALT Waterfront Kitchen, or Courtney’s Seafood. You can’t go wrong with any of these!

One last scenic drive will get you to Leonardtown, where the walkable downtown and free trolley mean you won’t have to get back in your car for the rest of your visit!

Check in to The Inn at Leonardtown, conveniently located right off the town’s central square, and get ready for a fun evening of exploring.

Day One Evening

There’s loads to see and do in Leonardtown, so we encourage you to walk around, explore, and see what catches your interest! Check out one of the shops like Marie & Nash for upscale gifts or Fenwick Street Used Books & Music. Visit Shepherd's Old Field Market to shop from over 90 ninety small businesses all under one roof!

When you start getting hungry for dinner, there are plenty of places to pick from around town. If you’re seeking an upscale dining experience, try Sweetbay or The Front Porch. If something more casual is your style, check out The Rex or Olde Town Pub for classic pub fare.

Wind down the evening at Leonardtown Wharf Park. Grab a tasty ice cream cone from Frog Town and watch the sunset over the water. Or better yet, watch it from the water on a sunset cruise with Fish the Bay Charters! Find the sunset cruise schedule here.

Head back to your room at The Inn at Leonardtown for a well-deserved night of sleep!

Day Two Morning

Go for a relaxing morning stroll and make your way to one of Leonardtown’s coffee shops or bakeries. Social Coffeehouse, Flour Donuts and Bakery, Kneaded Baking Co., and Botanic Café are all great options!

And that wraps up an awesome 24 hours in St. Mary’s! There’s so much more to explore, so consider staying for a weekend or even a week on your next visit. We’ve got you covered with places to stay and things to do when you return.

Stay tuned for more itineraries and trip ideas from Visit St. Mary’s MD! Follow us on Facebook and Instagram to be the first to know when we post new blogs.