Rock Hall Pirates & Wenches Fantasy Weekend 2016

Were you a child who enjoyed dressing as a buccaneer for Halloween? Do you find yourself watching and re-watching the Pirates of the Caribbean movies? Maybe you even found yourself empathizing more with Captain Hook than with that pesky Peter Pan. If you have any interest whatsoever in the world of piracy, then you won’t … Read More

5 Fun Summer Activities in and around Chestertown, MD

With our newly announced Sizzling Summer Savings, July is the perfect time for a Great Oak getaway here in Chestertown, Maryland. Summer is always full of excitement, and Chestertown is no different, hosting a variety of activities from golfing to hiking to swimming. Keep reading for a list of 5 fun summer activities for 2016: … Read More

4th of July Festivities in and Around Chestertown, MD

Independence Day 2016 will be here soon, and Kent County, Maryland is gearing up for a day of parades, live music, cookouts, and of course, fireworks. From Georgetown to Rock Hall to Chestertown, there is a great selection of Maryland events to bring out the patriot in you and celebrate the freedom that we are … Read More

3 Reasons to Take a Midweek Vacation at Great Oak Manor

Summer vacation has come to an end, and with the next holiday being so far away, you may find yourself trudging through the workday and reminding yourself that the weekend will be here soon. But don’t be satisfied with workday plodding! Break up the monotony of your weekly routine with a mid-week vacation that will … Read More

Chestertown’s Music in the Park Summer Concert Series

“It was June, and the world smelled of roses. The sunshine was like powdered gold over the grassy hillside.” ― Maud Hart Lovelace June has arrived, the weather is warm, the water is sparkling, and Chestertown, Maryland is bursting into activity. One much anticipated activity is Chestertown’s “Music in the Park” Summer Concert Series. Let’s … Read More

Crab Quiche Recipe from Great Oak Manor

One of the best parts about staying at a bed & breakfast is the food.  Here at Great Oak Manor, you’ll have the chance to indulge in everything from vegetarian breakfast Stromboli to fresh fruit and quiche. And speaking of quiche, we have a mouthwatering recipe for you to enjoy as a small taste of … Read More

The Chester River Wine & Cheese Company

M.F.K. Fisher, a prominent food writer and founder of the Napa Valley Wine Library once stated, “Wine and cheese are ageless companions.” We happen to agree and can find no place better to demonstrate this assertion that the Chester River Wine & Cheese Company right here in Chestertown, Maryland. “Located in the vibrant Arts & … Read More

3 Reasons to attend the Chestertown Tea Party Festival

If you caught our last blog, then you’ve already seen mention of the upcoming Chestertown Tea Party Festival, a celebration of Chestertown’s very own version of the Boston Tea Party. According to the rich oral history of our town, “on May 23, 1774, the local chapter of the Sons of Liberty…boarded the brig [Geddes] by … Read More