There’s never an offseason for romance at Osprey Point, an elegant, waterfront haven in Rock Hall, Maryland, the “Pearl of the Chesapeake.” Rock Hall, while quaint, remains one of the most desirable romantic getaways in Maryland, primarily because of its historical significance, picturesque beauty, and proximity to several metropolitan areas, including Baltimore, Washington D.C., and Wilmington. And nothing encapsulates the town’s charm, beauty, and convenience more than Osprey Point.
Embrace Winter, Embrace Each Other
Because Rock Hall averages approximately 13 inches of snowfall each year, the topography often transforms into a snowy winter wonderland, complete with ice crystals, hoarfrost, and icicles. Thankfully, the temperatures never reach “intolerable” levels. Thus, a little outdoor exploration on our 30-acre estate (or the nearby Eastern Neck National Wildlife Refuge) should be on the itinerary. After all, a healthy dose of winter hiking inside Eastern Neck in search of tundra swans, bald eagles, and great horned owls will do the soul some good—and it’s undeniably romantic, especially when snowflakes are gently swaying from the clouds above.
Learn about the region’s absorbing history at Waterman’s Museum or the Rock Hall Museum before meandering into the Rock Hall Village and Main Street, home to the Eastern Shore Wreath Co., Smilin’ Jake’s Casual Attire, Vintage Picnic, Get the Scoop, and the Java Rock Coffeehouse. For more date night ideas, please take a peek at our comprehensive Rock Hall guide.
Fine Dining, Award-Winning Vino, and Casual Elegance
Osprey Point Restaurant prides itself in offering fresh coastal cuisines, an eclectic mix of award-winning wine labels, and supreme hospitality—all in a casual, elegant setting. The seasonally-inspired menu utilizes locally-sourced ingredients from the earth and the sea. Start each meal with an hors d’oeuvre, such as the fried calamari or the tuna tartar. Entrees range from seared scallops to filet mignon and grilled salmon with roasted cauliflower puree. It’s a culinary voyage worth revisiting time and time again. Pair your romantic dinner with a bottle of fine wine from one of Europe’s prized regions. And, lastly, complete your meal with a homemade dessert from our house pâtissier, such as the crème brûlée or the chocolate silk torte with a sour cherry compote.
Romantic Getaways in Maryland: Osprey Point
Start and finish each day in the luxury accommodation of your choice, including Bolero, Escapade, or Windigo. Each uniquely-designed suite features distinctive decor, ultra-comfortable furnishings, hand-crafted artistry, and views of the grounds. We couldn’t think of a better place to relax (or unthaw) after a full day of exploration, shopping, and fine dining. Watch a performance in the comfort of your guest suite via The Mainstay’s live stream. Or, better yet, when COVID-19 fades, purchase tickets to see a local performance.
There’s still time to book a last-minute New Year’s Eve getaway. While this year’s “Rock Hall Crawl” will no doubt be a little different, it’s sure to be yet another colorful extravaganza highlighted by annual traditions, giveaways, competitions, and fireworks.