The Anchorage

b&B established spring 2019

what our guests are saying

“Wonderful hosts, beautiful place to stay, and very quiet. Michelle and Woody gave great guidance on where to ride bikes, restaurants, and local activity”

“Tempted to keep this place a secret but Woody and Michelle deserve better. If you’ve been fortunate enough to discover The Anchorage, stop reading now and book”

“We had everything we needed for the perfect weekend getaway”

“Gorgeous waterfront views that greet you splendidly from morning’s first light”

“You made us feel as if this was our home too”

“Gracious and friendly hosts, lovely room, fantastic property - a 5 star experience!”

“The room was beautiful and spotless and the bed very comfortable”

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, which has been called “the noblest watercourse on the Eastern Shore.” James Michener based his classic novel Chesapeake along the Choptank River and wrote after boating up the river in 1976 that he “saw a truly delightful sight: mile after mile of river bank on which not a sign of human habitation was visible”.

Located in Talbot County near the small historical town of Trappe, the Anchorage is also in close proximity to other charming towns and villages including Easton, Oxford, St. Michaels and Cambridge. Film, food, art, music, water activities, festivals and triathlons are just some of the events and activities that await you. There is also plenty of room for quiet and calm if you just want to sit on the beach while relaxing and taking in the beauty of the Choptank.

Our common areas in the B&B include a comfortable dining room for breakfast with a fireplace, and a large porch with a sitting area overlooking the water. There is also a smaller seating area outside with a grill if you want to eat in. Our new addition is a small outdoor art lounge, where you can paint, read, or bring a cocktail to the repurposed bar.

With over 12 acres to explore, enjoy the shady Picnic Grove with a book in the hammock and watch the birds and wildlife. Or enjoy the shady vista overlooking the river while eating crabs. On a cool evening, there may be a bonfire going. There is also comfortable seating on the beach with plenty of shade or you can search for sea glass. Our guests have fished right off the beach, or taken the kayaks out for a spin. And don’t miss the spectacular sunsets!

So…if you are looking for a peaceful getaway with quaint nearby towns, modern and newly updated rooms, come visit us!

We look forward to your stay.

Michelle and Woody