My mom started a fun tradition of road tripping to new places around the country together for my birthday. We have done this for as long as I can remember - some past destinations included Lake George in New York, Savannah, GA, and this year we crossed the Bay Bridge to a little town on the Eastern Shore - Chestertown, Maryland. We stayed at the Great Oak Manor, a bed and breakfast full of history and with waterfront views of the Chesapeake. This b&b is not only great for vacation, but it's a perfect venue for a Maryland wedding! I photographed some of my favorite details around the property to highlight this amazing location tucked away in Kent County. We spent mornings in adirondack chairs overlooking sailboats in the water; afternoons kayaking amongst cranes, woodpeckers, and ducks; and evenings lying in hammocks under the old trees, listening to the hoot of owls. They have fire pits for s'mores, bicycles to ride into town, and a private beach with kayaks and stand up paddle boards to enjoy. We even visited a nearby winery, Crow Vineyard and Winery, and took a sailboat ride at sunset with Blue Crab Chesapeake Charters complete with birthday margaritas! A perfect trip.