Much like a cast of characters in a Southern novel, Leonardtown’s dining spots each tell a distinct story. The historic waterfront whispers through white-tablecloth elegance, while Main Street bustles with cozy tavern charm. And yes, there’s always that one spot where the crab cakes are legendary enough to spark friendly debate. Whichever flavor of Southern Maryland you crave, you’ll find it here—from Chesapeake classics to modern twists. Read on for the 11 best restaurants in Leonardtown.
Ironwood Grill
$ | (301) 475-7228 | WEBSITE
If Leonardtown is the land of golf courses, Ironwood Grill makes a strong case for pub-style dining. Everything here is served with a view, and because the restaurant is so popular, they’re hosting community events like the annual Christmas tree lighting. There are two seating options: indoor tables and outdoor patio seating overlooking the golf course, both with that relaxed country club atmosphere.
The menu is consistently satisfying, and ranges from standard pub fare to deli-style sandwiches like the standout fried chicken sandwich and the recommended Reuben. Keep an eye out for sides featuring those classic McDonald’s-style french fries, especially when paired with the taco salad.
Sweetbay Restaurant & Bar
$$$ | (240) 309-4148 | WEBSITE
This inviting bi-level spot features a concise but delicious menu and, depending on which day you go, a lively atmosphere. With a spacious interior full of well-decorated seating and an outdoor patio that adds to the appeal, Sweetbay Restaurant & Bar is about as close as you can get to a perfect brunch or casual dining experience without leaving Leonardtown.
Dig into stuffed mushrooms from the appetizer list, creamy crab soup, and a wagyu burger that punches above its weight class, all while debating which safe but limited drink you’d order for a birthday celebration or casual meal.
Frog Town Ice Cream
$ | WEBSITE
There are two ways you can do Frog Town. You can wait in line, place an order, sit on a bench in the grass area, and then watch the serene water view while enjoying your scoop. Or, you can place an order over the phone, pick everything up with no wait, and dig into it all in the privacy of your car. Unless you’re someone who enjoys crowds, the latter is the way to go.
You’ll get the same cups filled with dark chocolate raspberry truffle or maple walnut, but without being jostled by people still in their park stroll gear and squeaky sneakers.
Botanic Café
$ | (240) 309-4129 | WEBSITE
If you’re looking for a cozy spot in Leonardtown—or on the days when you want your lunch elevated beyond the usual sandwich routine—head to Botanic Café. The menu offers more than simple café fare, with creative vegetarian options and a variety of other dishes like the popular Buddha bowl and turkey cranberry and brie panini. Grab a seat near the front windows for a charming view of the local businesses, and don’t miss the coffee, which features unique options like the lavender honey latte.
Jubilee Farm
Lately, finding a wedding venue that feels both private and picturesque is as rare as finding a quiet corner in a crowded city park. But that’s exactly what Jubilee Farm delivers, with three separate locations for the ceremony, cocktail hour, and reception. That’s far from the only reason to book this Southern Maryland gem, though—there’s also the kindness and hospitality of owners Jim and Maggie, who make the planning process a breeze.
Plus, there’s the recently renovated reception barn that elevates the space, the agricultural charm that enchants guests, and the overall atmosphere that perfectly captures the essence of the region. And there’s the fact that the staff is incredibly helpful and ensures every wedding is a truly memorable experience.
Smash House
$ | (240) 538-2245 | WEBSITE
If your goal is to eat a perfectly smashed burger with crispy edges in Leonardtown, but you prefer a no-frills atmosphere and generous portions, Smash House is the place for you. Beyond the unassuming storefront, which might be described as a hole-in-the-wall, you’ll find a straightforward counter where you can place your order.
Whatever else you try—the well-seasoned Oklahoma Smash Burger Combo or any of their other offerings—tack on a side of smash fries, those crispy potato wedges that could easily do for a meal on their own. There’s also a straightforward approach to service, with friendly staff who make the experience personable.
The Slice House
$ | (301) 997-6577 | WEBSITE
The Slice House is for the nights when you want something a little more exciting than plain cheese pizza. Beyond daily favorites, the shop offers creative options like the chicken cilantro with fresh herbs, or the eggroll pizza with crispy cabbage—plus a full menu of unique specials, like the stuffed ham pie, which has become a favorite for those seeking something different. Get delivery, or order at the bar and eat at one of the umbrella-shaded outdoor tables in the lively courtyard.
Ledo Pizza
$ | (301) 475-9280 | WEBSITE
This family-friendly pizza joint in Leonardtown is a reliable spot for Italian classics like pizza and pasta. The menu features crowd-pleasers such as their signature pies and chocolate dessert that hit the right notes for both kids and adults. The pizza—a crispy crust topped with quality ingredients and baked just right—is something you should try at least once.
It’s rarely packed here, and even during a Friday lunch the tables were mostly empty, so you can come without a wait or plan for a quick meal. The service is so-so, with food arriving promptly but the overall experience feeling a bit lackluster, and the tables could use better cleaning between guests. Still, it’s a decent casual option when you’re craving straightforward Italian fare without the fuss.
Fitzie’s Marina & Pub
$$ | (301) 475-1913 | WEBSITE
Until recently, there wasn’t a place to sit outside on a sprawling waterfront patio with your toes in the sand and sip frosty beers from a lively Tiki bar. Thankfully, Fitzie’s has been serving up first-class food with a fun, family-friendly atmosphere for years. The seafood buffet offers crab balls, shrimp, and fried oysters, but also more creative dishes like crab pizza and shark bites.
The bar menu has a solid selection of cold drinks, and any fried basket can be upgraded with extra zucchini fries for about three dollars. Go with the whole family and find a table overlooking the beautiful water views, surrounded by the flip-flop and sunhat crowd enjoying arcade games while the kids play.
Kneaded Baking Company
$ | (301) 381-2525 | WEBSITE
Long before the days of artisanal bakeries charging $8 for a single croissant, there was Kneaded Baking Company. Since opening, this quaint Leonardtown bakery has been drawing a sweet-toothed clientele with its menu of fresh bread, quiches, tarts, and macaroons. Pop in for a morning latte and cinabun, or for an afternoon treat while browsing the town square.
