Engagements on the Eastern Shore

You’ve finally met that special someone and you’re ready to pop the big question! Congratulations! Now, it’s time to plan, what will surely be, one of the most special days in your loved one’s life.

The story of your proposal will be told hundreds of times over – no pressure or anything! You will happily share it with your friends and family, and mom and dad will no doubt brag about it to their friends too.

We know planning a proposal is an exciting – yet stressful – time and Great Oak Manor wants to help you plan a romantic proposal that you and your love will remember for a lifetime.

Imagine driving down charming country roads that lead to the manor, which offers a few acres of grounds to explore, intimate gardens, a sensational view of the Chesapeake Bay, and a private beach. Spend a few hours walking the grounds, sitting on a beach, or get cozy in the library next to a roaring fire in the colder months. Explore Kent County and then return to the manor in the evening to celebrate your engagement.

We’ve selected some of our favorite proposal locations that will make for the most memorable engagement. Maryland’s Eastern Shore offers beautiful scenery (from forests to beaches), quaint little towns, wildlife retreats, picturesque waterways – all of which can act as the backdrop for your special day:

Crow Vineyard MarylandChesapeake Wine Trail

From Northeast to Ocean City, MD, the Chesapeake Wine Trail boasts 18 vineyards – three of which are in Kent County: Crow Vineyard and Winery, Clovelly Vineyard, and Cassinelli Vineyards and Winery. Not only will you enjoy great wine along the trail, you will find delightful, romantic spots where you can ask that special question.


This quaint little town, which served a major port of entry during colonial times, is full of history. Walk down the brick sidewalks to browse through the unique stores or visit the old colonial residences. After an afternoon of shopping (or proposing), enjoy some delicious Maryland seafood at one of the many restaurants or enjoy a glass of wine at the brand new winery – Casa Carmen.

Rock Hall

Known as the “Pearl of the Chesapeake,” Rock Hall is waterfront community on the Chesapeake Bay with miles of shorelines and many marinas. A vibrant arts culture resides in this seaside town and people come from all over for good music and steamed crabs!

Bike the Chesapeake Country National Scenic Byway

For our more active guests, we recommend biking the Chesapeake Country National Scenic Byway (of course, you can drive it too!). Picture yourself cruising down wide roads with little traffic, passing beautiful farmlands and lush forests, as you head to waterfront destinations. One of the best sections of the Byway is located in Kent Country. This 40-mile stretch offers plenty of scenic places to get down on one knee – from Georgetown (on the Sassafras River) to Chestertown, through Rock Hall, and then to the Eastern Neck National Wildlife Refuge on the Chesapeake Bay.

Take a Boat Ride

The Chesapeake Bay has gorgeous views from land, but just imagine what you can see on the water! Plan a [private] cruise around the bay for an unforgettable proposal. There are several charters in the area including: the Chester River Packet in Chestertown, Blue Crab Chesapeake Charters, Haven Charters, and Shardana Sailing Charters, all out of Rock Hall.

For more information or to book your stay at Great Oak Manor call 410-778-5934.