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

2017 Labor Day Events

Friday, September 1 Head to Chestertown for First Friday. Enjoy late shopping hours, gallery exhibit openings, and a variety of delicious dining options. Saturday, September 2 – Sunday, September 3 Visit Rock Hall, MD for their annual Labor Day festivities. On Saturday, meander around the town and check out the vendors and activities.  At 8 … Read More

Star Spangled National Historic Trail

Nestled on the Eastern Shore of the Chesapeake Bay, Kent County is the perfect destination for any history lover who’s is looking to enjoy a historically-rich vacation. One of the best tours is the Star Spangled National Historic Trail, which depicts the history of the War of 1812 in Kent County. There are several important … Read More

Fun Facts about Labor Day

Did you know… Labor Day celebrates the contributions of the millions of men and women in the US workforce. The first US Labor Day was planned by the Central Labor Union and held September 5, 1882 in New York City. On this day, nearly 10,000 workers took unpaid leave and marched from City Hall and … Read More

Why We Love Chester River Wine & Cheese Company

Chester River Wine & Cheese Company: A Cheese Lover’s Paradise Quite simply, if you are a cheese lover, the Chester River Wine & Cheese Company should be your first and last stop while visiting Chestertown. A specialty food shop that offers both international and domestic wines, charcuterie and pate, as well as cut-to-order cheese, it’s … Read More

Romantic Eastern Shore Weddings Start Here

Romantic Eastern Shore Weddings at Great Oak Manor For a once in a lifetime event, you need a once in a lifetime venue. Here on the eastern shore of Maryland, Kent County is the idyllic area spot to celebrate a monumental day in both of your lives–your wedding! Waterfront views and stunning countryside are an … Read More

Birding in Kent County, Maryland

Bird lovers, unite and come to the Eastern Shore! Birding in Kent County is plentiful! From Snow Geese, Canadian Geese, 24 species of ducks, sparrows, blackbirds, terns, Great Blue Herons, and eagles, you’ll have more than 300+ species to enjoy! We invite you to start your day with us here at Great Oak Manor before … Read More

10 Events and Activities in 2017

  January has nearly flown by, and if it’s any indication for the year to follow, 2017 is bound to be a whirlwind year.  We’ve already gotten our feet wet planning out the rest of the Winter season with fun events and a Winter Spa Selection.  As you begin planning your 2017 weekends and vacation … Read More