Nine Reasons to Spend Christmas on Maryland’s Eastern Shore

The holiday season is almost here… in just a few short days, the jack-o-lanterns and witches will be replaced with snowmen and Santa Clauses. Many people travel for the holidays, whether it’s to visit family, mix up the same old traditions, or indulge in an amazing experience. This year, mix it up and visit Great … Read More

Rent Out Great Oak Manor: Weekend Packages

Great Oak Manor is a charming Georgian estate located on the Eastern Shore, just minutes from historic Chestertown. No matter the season, Kent County offers beautiful scenery and plenty of fun attractions for you and your friends or family, including wine tours, bird watching (visit the tundra swan that drops by the Chesapeake Bay during … Read More

Enjoy a Delicious Thanksgiving Feast at Great Oak Manor

The holidays are a great time to take a few minutes to be grateful for those people and moments that we’ve had the pleasure of experiencing in our lives. While it may be a great time to reflect or catch up with old friends, they’re definitely not relaxing. From meal planning to gift buying (and … Read More

Celebrate the 2017 Holidays at Great Oak Manor

Holidays can often be stressful affairs between the gift giving, cooking, and cleaning. Why not treat yourself to a break this season and spend Thanksgiving or Christmas on Maryland’s Eastern Shore. Imagine waking up in the morning knowing you don’t have to cook and enjoying all the holiday splendor the Chesapeake Bay has to offer. … Read More

Eloping on the Chesapeake Bay

Gone are the days of only eloping at city hall or in Vegas. No matter the size of your wedding (two or two hundred) there is still a small bit of planning involved, so it can be as simple or as grand or as intimate as you want. Some people dream of a big church … Read More

A Note from the Innkeeper – September

The most rewarding aspect of our job as innkeepers is meeting all of our wonderful guests. This is why we do what we do. We have met some of the most interesting people of our lives to date. We love their stories and are fascinated by their lives and travels. So a day without guests … Read More

Six Reasons to Plan a Fall Adventure on Maryland’s Eastern Shore

Labor Day has come and gone, which means the unofficial end of summer. Before we know it, Pumpkin-flavored goodies will adorn grocery store shelves, the heat will begin to dissipate and the green leaves will give way to beautiful red and gold hues. It’s never too early to plan your fall getaway to Kent County, … Read More

Downrigging Delight: A Chestertown Festival Along the Bay

If you’ve been keeping up with our past few blogs, you know that Kent County is a hub of activity in Maryland. From a Pirates & Wenches Fantasy Weekend to a Harry Potter Festival, we know how to celebrate the worlds of history and fantasy. (If you missed or will be missing either of these … Read More