Letter from the Innkeeper – February

So here it is February already and our thoughts turn to love and celebrations of love. There are so many kinds of love to express. Richard and I have been at Great Oak Manor for 11 months now and we just love this place. What is not to love about sitting at one’s desk or … Read More

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 … Read More

Celebrate Love at Great Oak Manor this February!

If you’re looking for a thoughtful and unique idea for Valentine’s Day this year, consider spending a relaxing weekend on Maryland’s Eastern Shore. Great Oak Manor is a romantic bed and breakfast, nestled on a bluff overlooking the Chesapeake Bay. Whether you’re looking to relax with a book and a glass of wine by a … Read More

Why You Need to Visit Maryland’s Eastern Shore after the Holidays

The holidays are over. The past few weeks were spent decorating the tree, baking cookies, squinting at the computer screen as you searched Amazon or Wayfair for the perfect gifts, reminding your (grand)children that Santa is watching them, shopping for holiday food, gift wrap, and other supplies, and wrapping an endless pile of presents. The … Read More

Holiday Shopping in and around Chestertown

The holidays are here again… and you know what that means! Shopping! Don’t strain your eyes pouring over websites. Avoid the stress of the malls and shopping centers. Instead, support local vendors and give your friends and family unique, heartfelt gifts from Chestertown. Here are some of our favorite shops in and around Chestertown: Bloomin’ … Read More

Baked Cranberry Oatmeal

  Ingredients 3 c. old-fashioned oatmeal (not quick cooking) 1½ c. brown sugar, divided 1½ tsp. baking powder ¼ tsp. salt 1 tbl. finely grated orange zest (zest of about one orange) 2 tsp. cinnamon, divided 3 c. almond milk 1 tbl. vanilla extract 2 large eggs 2 c. fresh cranberries, divided ¾ c. all-purpose … Read More

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