Leonardtown, Maryland, blends rich history, waterfront revitalization, and a vibrant arts scene. With historic sites, new restaurants, parks, festivals, and cultural programs, it fosters community engagement, tourism, and economic growth while preserving its unique small-town character.
SOCIAL Coffeehouse & Cocktail Bar
A great breakfast pick — try The MVP (egg, cheddar, bacon or sausage on a croissant) or the Maryland Bagel with their signature crab‑dip and Old Bay.
See MoreMcIntosh Park
Small, family-friendly park with open green space, playgrounds, and walking paths. Great for a quick stretch or picnic, and quiet enough to catch birds or read under the trees without crowds.
See MoreAntoinette’s Garden
This wine‑and‑coffee café doubles as a soulful brunch spot. Order the Shrimp & Grits (creamy grit cake, buttered shrimp) or the Southern Comfort French Toast — plus a mango mimosa if you’re feeling festive.
See MoreBrüdergarten (Brü)
Brüdergarten is a relaxed beer garden inside Shepherd’s Old Field Market with over 20 taps, snackable fare, and outdoor games. Grab a bratwurst with a pretzel on the side—it’s classic and pairs perfectly with their rotating craft beers.
See MoreShepherd's Old Field Market
Shepherd’s Old Field Market is a bustling gourmet market and café with a mix of local groceries, wine, and prepared foods. Try the fresh-made quiche or grab a sandwich from the deli case—it’s reliably flavorful and filling.
See MorePort of Leonardtown Winery
Port of Leonardtown Winery offers handcrafted wines in a relaxed tasting room with waterfront views. Try their Sea Breeze White or Sweet Blush—perfect for sipping on the patio while enjoying the riverside scenery.
See MoreLeonardtown Wharf Park
Leonardtown Wharf Park is a scenic waterfront spot for walking, picnics, and events. Bring a blanket and a snack, or grab a coffee nearby and watch boats drift by—sunsets here are especially worth the visit.
See MoreThe Rex
Housed in a former movie theater, The Rex is a lively bar-restaurant with comfort food and live music. Try their Old Bay Chicken Wings — salty, crispy, and a fan favorite.
See MoreSweetbay Restaurant & Bar
Sweetbay doubles as a chic drink destination — their cocktail menu is sharp, imaginative, and well curated. Try the Fig Off (bourbon, fig preserves, lime) or the smoky Rye Old Fashioned for a rich, layered sip.
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