Couple and their dog watching the sunset over the water

A Letter from the Innkeepers – April 2018

  Spring is here – well, almost here. This time last year we were just settling in and rushing around to make spring happen. This year we are super excited about some wonderful changes that are taking place around here. Richard has been working all winter on the inside of the Manor, painting and sprucing … Read More

View from an old, wooden sailing ship

Chestertown Tea Party Festival 2018

In the spring of 1774, when news of the port of Boston’s closing reached Chestertown, the citizens met to determine what actions should be taken in response. They forth a list of grievances, which became known as the Chestertown Resolves, which made it unlawful to buy, sell or drink tea that came from England. According … Read More

Where to Eat Dinner (or Brunch) this Easter

This Easter, enjoy divine culinary experiences across Kent County. We’re not cooking this Easter (we need a break on at least one holiday!), but there are plenty of dining options on the Eastern Shore. Check out a few of our favorite spots: Barbara’s on the Bay Betterton, MD Open for Brunch from 10:30 a.m. to … Read More

Upcoming Festivals in Kent County

Maryland’s Eastern Shore offers visitors many family-friendly attractions and activities on the water. In addition boating, kayaking, crabbing, and cycling, Kent County hosts several exciting festivals throughout the year. Here’s a sneak peak at what’s happening this spring!  Dogwood Festival of Galena May 5, 2018 Visit the annual Dogwood Festival in Galena, a picturesque little … Read More

Red Velvet Sweetheart Pancakes with Cream Cheese Glaze

Ingredients: Glaze 1 4 oz. pkg of cream cheese, softened 1 cup confectioner’s sugar, sifted 1 tsp. vanilla 1 tbsp. milk, as needed Pancakes 1 ½ c all-purpose flour 2 tbsp. white sugar 2 tsp. baking powder 1 tbsp. unsweetened cocoa powder 1 tsp. salt 2 eggs ¼ c milk 1 c buttermilk 1 tsp. … Read More

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

COVID-19 Travel Information

We’re working hard to keep our guests healthy and safe, and are continuing to monitor the Coronavirus situation. Please click below for the latest updates. We are here for you!

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