Valentine's Planning Guide
Fall in Love with St. Mary’s County
Looking for a relaxing getaway to celebrate love this Valentine’s Day, St. Mary’s County is your destination for romance. The area offers it all, from unique stays to extra sweet desserts and even a cozy cat cafe. Maryland’s Original Destination is the perfect backdrop to fall in love. Here is your ultimate guide to planning a Valentine’s Day weekend!
Date Night To-Dos
There is so many fun events and activities going on throughout the county!
One spot that always has something going on is the motel and restaurant Pier450. Named on the 2025 Romantic Hotels Northeast US List from Getaway Mavens, Pier450 is a beach-chic destination spot along the waterfront in the southern-most tip of St. Mary's County. A rejuvenated 1940s-era fishing camp, The Quarters motel has eight uniquely curated rooms, each with a different theme and beautifully decorated interiors. Outside, you’ll find an extensive gathering porch and as you wander down the short boardwalk to the beachfront, you’ll see chairs with firepits, an outdoor bar, and kayaks available for motel guests — and a stunning sunset view.
For Valentine’s Day Weekend, they will be offering an exclusive dinner menu and a pasta making course (wine included) with one of their head chefs! If you book a room at The Quarters on February 14th or 15th, your partner will be registered free of charge!
If you’re looking to spice up your trip with action, channel your inner Viking and master the art of axe throwing at Viking Axe Throwing in Leonardtown! At their location inside Action Lounge & Billiards, you'll learn how to safely and properly throw axes, ninja stars, and other throwing tools. Each session includes training before you start; once you get your first bullseye, you'll be hooked!
If relaxing is more your style, take a stroll around Historic St. Mary's City, Maryland's first capital with living history exhibits assembled across the landscape. While the outdoor exhibits are closed for the winter, it’s a great chance to explore the St. John’s Site Museum and gift shop, as well as the walking trails along the water.
The coziest option of all in St. Mary’s County is a date day trip to Meow Dyer Cat Cafe, one of the newest businesses to open in the area! Whether you're considering adoption, can't have a cat due to allergies, or live in a pet-restricted area, their cozy space is designed for you to relax and enjoy the company of adorable feline friends with select drink options.
Romantic Homes Away from Home
While Pier450 is a great option, the county has many places to getaway with your significant other. Swanendele Inn is an elegant, family-owned country inn nestled on the shore of the Chesapeake Bay and St. Jerome’s Creek. It was constructed in traditional Southern Maryland style, with wraparound porches and waterfront views from every window. The Suite and the largest room offer Jacuzzi tubs for two with a defined view of the water and sunset – each with a built-in Champagne sink. The house is furnished with the owner’s eclectic collection of artwork and antiques gathered from all over the world.
If you’re looking to be closer to all the action of Leonardtown, The Inn at Leonardtown is a boutique hotel offering a perfect walkable retreat to explore the area’s attractions and outdoor recreation. The hotel has well-appointed guest rooms that continue the hotel's stylish decor and offer a 55-inch flat-screen TV with premium channels, a microwave, refrigerator, Keurig coffee maker, desk with ergonomic chair, and more.
The Ultimate Pairing: Wine and Chocolate
Nothing goes with love better than chocolate and wine! The Port of Leonardtown Winery, the only co-op owned winery in the U.S. and part of the St. Mary’s Craft Beverage Trail, is known for its exceptional award-winning wines and wine tastings. The winery itself is a model of adaptive re-use as it is located in an abandoned state highways garage now remodeled into a warm and inviting space filled with local art.
Heritage Chocolates in Leonardtown features delicious in-house chocolates and candies including caramels, brittles, toffees and so much more. They provide quality products that local customers know and love, while continuing to develop exciting, new flavors with over 75 unique recipes.
If wine isn’t your thing, there are plenty of coffee shops to check out as well, including the comfortable and intimate St. Inie’s Coffee. This family-run coffee roastery provides fresh-roasted, responsibly sourced pour over and drip coffee as well as yummy treats. Their inviting community space features cozy seating plus books to browse and buy.
Table for Two
St. Mary’s County has lots of great places to eat - from seafood dives to sidewalk cafes to white tablecloth establishments. One of the more romantic options with stunning waterfront views is the Ruddy Duck Seafood & Alehouse. With its unique dishes, fresh seafood, and artisan-crafted beer from their brewery in Southern Maryland, enjoy a creative menu utilizing fresh local resources coupled with gracious service.
Looking for white table clothes and an elegant atmosphere? The Sweetbay Restaurant in Leonardtown serves steak, seafood, whiskey flights and more. Sweetbay is a catalyst to walkable Leonardtown’s revitalization through a great neighborhood restaurant.
Classic Italian food can be found at Noli’s Italian Cucina. Their authentic Italian dishes and baked goods come from recipes that have been passed on from generation to generation. One of their well-known dishes is pizza, as their dough is prepared in-house with imported San Marzano tomatoes and premium Wisconsin cheese cooked in a brick oven.
Weddings
If you love St. Mary’s County as much as we do, then considering hosting your wedding or vow renewal here! Home to the most beautiful historic, waterfront, and country destination wedding venues in Southern Maryland, find everything you need to plan your St. Mary's Destination Wedding.
