Springtime on the Eastern Shore : A 3-Night Itinerary

Nothing is quite like springtime in New England. The weather is mild, the flowers are blooming, and the outdoor adventures are available for you to enjoy. Right now is a great time for a getaway to Chestertown, MD. To make it easier, we’ve put together this handy itinerary so you can spend less time planning and more time having fun. Read on for our exclusive guide to a springtime getaway at Great Oak Manor on the beautiful Chesapeake Bay.

Picnic table with bay view with crab feast and beer

Day 1 : Arrive Ready to Indulge

Once you’re all checked in to your luxurious guest room, step outside to catch the beautiful sunset over the Chesapeake Bay while you whet your appetite for a meal that only Maryland can provide. Until March 31st we’ll be offering a romantic fireside dinner, so you can sip wine by the fire and relax while partaking in delicious cuisine made right here at the Inn. If you’ll be joining us in April, then you owe it to yourself to pre-book our famous Crab Feast! Served in our beautiful gazebo by the sea, it includes a dozen steamed crabs, corn on the cob, your choice of beer or wine, and an option to add a pound of shrimp. It’s the perfect way to get in the New England spirit and enjoy some authentic Maryland cooking. If you feel like venturing out for dinner instead, we can recommend several Chestertown restaurants that will not disappoint. We suggest trying the 9th best Italian restaurant in the state, Luisa’s Cucina Italiana, which serves delicious locally-sourced cuisine. Plus, they’re right in town, so it gives you an opportunity to pick up anything you may have forgotten to pack.

Couple on bikes looked at the ocean

Day 2 : Get Ready for Adventure

Wake up to a delicious homemade breakfast, which you can enjoy in our comfortable dining room, or outside on the terrace with its bay view if it’s warm enough. The lovely weather this time of year begs you to get outside and soak up some sun. At our bayside bed and breakfast, we provide four beach cruisers available for guest use to check out the local area. Or, if you’re a serious cyclist, bring your own bike with complimentary overnight storage so you can expand your riding experience. We’ll even set you up with a map and directions, so you can be fully prepared to go bike riding in Maryland. We’re also happy to arrange for a picnic lunch to savor on your journey! If you’re joining us in the warmer months of spring, we invite you to use our complimentary kayaks, canoe, or paddle boards from our private beach.

Couple at a table in front of a restaurant with map and camers

After your adventurous morning, we recommend that you slow things down a bit and check out historic Chestertown. Our charming downtown has lots of things to see and do including a local farmer’s market, unique shops, museums and art galleries, and delightful pubs and restaurants. After you’ve found some treasures, or maybe even tipped back a cocktail or two at a local distillery, return to the Inn to relax before dinner. We have several hammocks and Adirondack chairs to lounge in, so you can just soak up the sea air. Tonight for dinner we recommend that you try one of the classic Maryland waterfront restaurants like Barbara’s on the Bay, Waterman’s Crab House or Harbor Shack. Any one of these will provide you a distinct Maryland dining experience on the Eastern Shore.

Couple in a vineyard with glasses of red wine

Day 3 : Feel Fine with Water or Wine

Wake up again to an Inn-prepared breakfast where you can look forward to items like French toast, quiche or any number of our other delicious entreés – in addition to our granola, baked goods, and the best bacon you’ve ever had! With a full belly, you’ll be ready to take a tour of Maryland’s wine country! Believe it or not, the area produces fantastic vintages and has several friendly tasting rooms to sample the goods. Bring back a bottle or two to take home with you as a memory of your trip, or enjoy one with a private dinner for two at the Inn! We’ll prepare a custom menu with gourmet options like petit filet or locally sourced homemade crab cakes, along with a fresh salad, two sides, and a dessert!

Couple on a yacht holding the mast with their arms splayed out

For guests who have their sea legs and want to get out on the water, then plan your trip to the Eastern Shore in April so you can take advantage of all of the fun boating adventures on the Chesapeake Bay! Rent or charter a boat to see Maryland from the water – it’s breathtakingly beautiful. Whether you want to go fishing, crabbing, bird watching, or just take in a sunset cruise, we’ll be glad to help find you the perfect outfitter to suit your needs.

Breakfast on a table outside with a blue and white tablecloth with spring flowers in a vase

Day 4 : Relish the Memories You Made in Maryland

It’s your last day to enjoy our freshly-made and locally-sourced breakfast. Savor it a little longer, while you discuss the favorite parts of your trip. Use your time in the morning to walk our expansive lawn or dig your toes into the sand on our private beach. As you check out, we suggest that you take a look at your calendar and book your next trip to our Maryland bed and breakfast. If you loved your choice of room, you can certainly book it again, or feel free to try another one as each room is unique and offers different luxury amenities and views. On your way home, we encourage you to explore more of Kent County and enjoy your journey – discovering what makes the Eastern Shore of Maryland so special.