A Waterfront Getaway on the Choptank River

Escape to Tranquility: The Anchorage – Your Eastern Shore Retreat & Event Venue

The Anchorage, with origins back to 1800, is a Federal Telescopic Tidewater style B&B with waterfront views and six guest rooms situated on the beautiful Choptank River. We offer a relaxed and romantic experience on the shores of the river, which is part of the Chesapeake Bay waterway. Imagine waking up to water views, locally brewed coffee, and a hearty breakfast created with locally sourced ingredients, including vegetables and berries from our gardens. Whether you are are seeking a romantic getaway, a celebration, or simply a peaceful escape, The Anchorage can offer all of this. Enjoy contemporary guest rooms, a waterfront firepit, swimming pool, kayaks and spectacular sunsets. Its the perfect blend of natural beauty and comfort.

Located in Talbot County, the Anchorage is in close proximity to film, food, art, music, water activities, festivals and triathlons. Explore the nearby town of Cambridge, its cobblestone streets echoing with history. Wander through Oxford, where sailboats bob in the harbor. Visit Easton with brick lined sidewalks, boutiques, and the Avalon Theatre. And don’t miss St. Michaels, a postcard perfect village where time slows to a waltz. Each town is a gem on the Eastern Shore’s necklace and awaits your discovery. The property offers modern updates while preserving historic charm. Here, where the river meets the horizon, you’ll find peace and feel the stress of life fade away. We look forward in welcoming you!

Explore our Trappe, Maryland Bed and Breakfast:

Tour & Amenities

Guests enjoy 12 acres with hammocks, lawn games, beach access, kayaks as well as indoor spaces to relax.


6 guest rooms await your discovery. Each with private bath, Comphy linens, and breakfast included!


Have you been dreaming of a riverfront wedding or event? Our 12 acres are the perfect venue!

What Our Guests are Saying: “Stunning views and world class hospitality make for an unbeatable weekend getaway from the daily grind. Whether it’s waking up to Woody’s shockingly good breakfast or catching the sunset over the Choptank with a glass of wine and the water at your feet, there’s not much more you can ask for from the Anchorage B&B. Would love to return with my family some day.” Jimmy, Washington, DC