It’s one of the most memorable stories you will share for years to come—your engagement story. You will treasure every last detail from the words you say to the location you choose. The setting sets the tone for the special moment and the Eastern Shore of Maryland offers some of the most picturesque settings. From peaceful countryside meadows to the sparkling coastline. We have great proposal ideas for a magical Maryland proposal.

We’ve highlighted our picks for the top Maryland proposal locations that make for a picture-perfect engagement story.

Our Top Rated Maryland Inn & Cottages

Our elegant country estate is nestled on 20 acres of secluded open space and offers 6 romantic Maryland cottages and 7 guest rooms in the plantation house with an expansive wrap-around porch.

  • Surprise your loved one with a romantic weekend getaway in one of our private cottages. Have the room set up with roses and champagne so you can pop the question upon arrival.
  • Let us pack a picnic lunch for you and find a special spot on our private grounds. Romance him or her with a cheese and wine spread before you pull out the ring.

Plan a day trip to one of the attractions we highlight below and return to our quaint inn to celebrate with our proposal package.


Looking for an Eastern Shore outdoor adventure? Enjoy the water near our property.

Chesapeake Bay & The Eastern Shore

The Chesapeake Bay has some of the most stunning spots on the East Coast. There’s something so serene and enchanting about the “Land of Pleasant Living”. The area is sure to elicit a “yes” to your question.

Our top rated MD bed and breakfast is the perfect place for a romantic getaway.

Sailing on Chesapeake Bay

Plan a private day cruise on Chesapeake Bay. The sparkling waters next to a brilliant sunset scream romance and make for the perfect proposal. Blue Crab Charters offer a variety of cruise options, all of which include complimentary beverages.

Maryland Scenic Byway

The Brampton Inn is located on the Chesapeake Country Scenic Byway. Go for a drive along this iconic National treasure. It’s beautiful anytime of year, but for a fall proposal this is ideal with the stunning view of the changing leaves. Get specific driving directions and details about the National Scenic Byway.

Chesapeake Wine Trail

Whether you go for the scenery or the wine, the Chesapeake Wine Trail has plenty of charming, intimate spots to pop the question. The trail runs along the Chesapeake Bay and is rich with historic sites, wildlife, and quaint vineyards. Some of the Vineyards closest to us include:

  • Crow Vineyard and Winery
  • Clovelly Vineyard