There are so many reasons why we love the area surrounding our very own Chestertown, Maryland. The scenery is definitely one of them! Along the Eastern Shore of Maryland, you’ll discover beautiful foliage, winding country roads, and shimmering waters. The best way to see it all? A joyride, of course! Below, we’ve compiled just three of our favorite Chesapeake Bay scenic drives. For more of our favorite things to do in the region, be sure to access our free Travel Guide to the Eastern Shore of Maryland!
Some of the Best Chesapeake Bay Scenic Drives
The key to an unforgettable Chesapeake Bay experience lies within the small towns that surround it. Specifically, we’re fans of Maryland’s Eastern Shore: Where century-old farms, historic brick buildings, and, of course, stunning waterfront views win the day. Here, it’s perfectly acceptable to step out of your car and take in the view. At low tide, you can even find your very own fresh oysters lining the shore. No one will judge you if you pry one open for a true taste of life in the Chesapeake Bay area! Here are just a few of the places to embark on a scenic drive.
The Chesapeake Country Scenic Byway
One of the best (and most beautiful) Chesapeake Bay access points is the Chesapeake Country Scenic Byway. This winding route spans 419 miles between the upper and lower Eastern Shore of Maryland. Of course, it’s highly encouraged to choose a small section or two to explore! We recommend a section such as Chestertown to Kent Island, or Vienna to Wye Mills. No matter which route you decide to take, you’ll see gorgeous boatyards, farms, and waterfront vistas only found in our region!
The Great Chesapeake Bay Loop
Completing the Great Chesapeake Bay Loop is a perfect way to get the full Maryland experience! This stretch connects Southern, Central, and Eastern Maryland, so there’s plenty to see and do along the way. We recommend trying the following activities:
- Visit a maritime museum
- See a lighthouse
- See the Bay from the hull of a boat
- Try some quintessential Maryland seafood (the Maryland Crab and Oyster Trail is a great place to start!)
- Experience a Maryland wine trail
- See the Washington College
- See the Chesapeake Bay Bridge
- Check out fall foliage on the Eastern Shore
- Indulge in a delicious meal at one of Chestertown’s best restaurants.
End Your Journey at Brampton Inn in Chestertown, MD!
Tucked away within Eastern Maryland’s countryside is Brampton Inn, your perfect home-away-from-home! After seeing the sights on one of the best Chesapeake Bay scenic drives, you’ll want to take a detour and get some quality rest. Our bright, spacious guest rooms and cottages offer a lodging experience unlike any other. You’ll love our plush beds, large windows offering plenty of natural light, and premium amenities found nowhere else. Try “porch surfing” with us and see why Brampton Inn is the best place to sit back, relax, and make lifelong memories with your loved ones!