The Anchor Inn is a private waterfront wedding venue in Pasadena, Md. With only one wedding on the property at a time, Anchor Inn is the perfect intimate reception and ceremony site for your wedding. Steps away from the Chesapeake Bay, this venue sets the ambiance for a perfect day with friends and family. With a beautiful pier and covered ceremony options, you and your guests will be surrounded by the beauty of the Chesapeake Bay for your entire event. You'll also get stunning views of the Bay Bridge as well! If you’d like a free visit and consultation, please contact us today!

Our waterfront wedding venue lets the Chesapeake Bay provide a beautiful and elegant backdrop to your special day. Our goal is to exceed your expectations right down to the smallest detail because your wedding deserves no less. Our 30 years of experience planning all-inclusive weddings means that your journey can be stress-free. From relaxing in your bridal suite to photos on the waterfront, to dancing the night away – your day will be perfect! Consistent quality and diverse variety is the hallmark of our wedding catering service. Whether looking for an elegant multi-course dinner, or lighter afternoon fare, our extensive selection ensures you’ll find the perfect menu to compliment your event.

Our historic establishment is dedicated to providing an exquisite setting for all wedding-related occasions, including showers, welcome parties, rehearsal dinners, and more. Whether you envision an indoor affair accommodating up to 125 guests or an enchanting outdoor celebration for 150+ guests, both options offer stunning views of the Sassafras River. Our dedicated team is committed to ensuring that every detail of your event is flawlessly executed. We offer our guests a comprehensive wedding package, which can be further tailored to meet the unique requirements of their special day. From menus to personalized touches, we strive to exceed expectations and create unforgettable memories for you and your loved ones. To add to the historical experience, our 18th-century historic Kitty Knight Inn is located on the property and is available for guests to stay in. The inn has 11 recently updated rooms but still keep their historic charm that we are so well known for.

The Inn at Osprey Point is a sprawling estate in the charming village of Rock Hall, Maryland. This premier wedding venue and B&B is surrounded by 30 acres of lush landscapes and spectacular water views. It offers a variety of beautiful settings for any wedding day. The colonial-style inn caters to intimate celebrations while a one-of-a-kind waterfront tented reception will charm guests and loved ones. Whatever classic coastal vision couples have for their special day, the Inn at Osprey Point can make dream weddings come true. Please reach out for the full wedding package including food and bar choices that are available. With catering, bar, a full staff, and day-of coordination, your wedding is bound to be stress-free with Osprey Point!

Located in Rock Hall, Maryland, our properties are the ideal setting for any waterfront event. With five guest buildings totaling 21 rooms and suites, plus a private full-house rental, we know what it takes to make your special day a memorable one. Consider booking us for your wedding, elopement ceremony, reception, rehearsal dinner, class or family reunion, business event, fitness or health retreat, hunting trip, friends weekend, holiday party and more.

Great Oak Manor sits on the banks of the Chesapeake Bay on Maryland's Eastern Shore. The Georgian Mansion has twelve large guest rooms and a Carriage House. Because we are on the Bay, most weddings are waterfront on our expansive lawn with tented receptions. Smaller weddings and receptions might be held in our Conservatory.