Trip Ideas

Weekend Escape To Historic Leonardtown

Let us help you plan the perfect weekend escape in Downtown Leonardtown. Enjoy dining, shopping, history, wine and more!

Looking for a great place to escape for the weekend? Historic Leonardtown, in the heart of Southern Maryland, is a short drive from DC, Baltimore, and Annapolis and has so many great things to do, see, and taste. Our free concierge planner will help you set up the perfect weekend getaway close to home - any time of year! We will help you plan the perfect trip, make sure you get VIP treatment while you are here, and give you complimentary welcome gift basket.


Sample Itinerary


10 a.m. – Check in at the Leonardtown Visitor Center and pick up your VIP welcome basket full of treats from our local artisans. Our team will confirm your itinerary and make sure to get VIP treatment all weekend!

10:15 a.m. – Take advantage of the complimentary early-bird check in at the The Inn at Leonardtown. This brand new hotel features large, comfortable rooms set in the heart of the historic town so you can park your car and your belongings before venturing out for the day. Check your pillow for a special treat.

10:30 a.m. – Grab a cup of coffee and a pastry from Social Coffee House. Well known for their creative drinks and mimosa towers.

11 a.m. – Explore the shops on Fenwick street before heading to the Wharf for a short walk in the park. North End Gallery is the oldest art gallery in St. Mary's County and features fine art and jewelry from Southern Maryland’s best artisans and Fenwick Street Used Books and Music Store is full of treasures you won’t want to miss.

12 p.m. – Leonardtown Wharf Park is just a few short blocks away from Fenwick street. The small waterfront boardwalk is beautiful year round and the park has a pavilion and playground that make it a nice destination for families, couples and friends alike. Enjoy a stroll or, if you want, kayaking and paddle boarding from the wharf is also available and you can purchase rentals from Patuxent Adventure Center. Our local outfitters will be ready to help you.

12:45 p.m. – Grab a piece of pizza at The Slice House the area’s newest and most popular pizza joint. After lunch stroll over to Heritage Chocolates for a decadent dessert of local handmade chocolate and gelato.

2 p.m. – Stop in for a special guided tour at the Old Jail Museum. Built in 1876, this historic building is home to the oldest sheriff’s office in the nation and features cells where prisoners were once segregated by gender and race. We will help you set up your reservation for the tour.

3 p.m. – Continue exploring Leonardtown’s many small businesses at Shepherd's Old Field Market. The 2-story converted industrial building houses almost 70 shops full of local crafts and gourmet gifts. Stop by Botanic Coffee Shop and Deli on the first floor to grab a mid-afternoon pick me up.

4 p.m. – Feeling sharp? Why not end the day with an Escape Room Conveniently located between the market and the hotel, Escape Rooms Southern Maryland always has two exciting adventures to unlock. Let us help confirm your reservation for this fun activity.

6 p.m. – Dinner at Sweetbay Restaurant and Bar. You will love the food this DC Restaurateur brings to town while enjoying the safe and lively fine dining environment. We will help set up reservations for your dinner.


10 a.m. – Hop in your car or walk a few blocks over to The Front Porch. Their brunch is legendary and the historic Sterling House where the restaurant is located is filled with old-world charm. We will let them know you're coming and help with reservations.

11:30 a.m. – Hunt for vintage treasures at the Leonardtown Maryland Antique Center, just a short drive up the road from Leonardtown. Pick you way through aisle upon aisle of Collectibles, Furniture, Jewelry, Home Goods, and more.

12 p.m. – Just a stone’s throw from the Antique shop is the Port of Leonardtown Winery – the perfect place to pop in on your way out of town. Enjoy award winning wine at the first commercial winery in St. Mary's County and grab a few bottles to take home. The fabulous owners have a parting gift for you.

Let us help you put together the perfect weekend getaway. Contact Mary Wagner at, 804-410-4166, or fill out the form in the link below.

Speak with our concierge now

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