If you’re dreaming of a road trip full of scenic beauty, waterfront charm, and small-town hospitality, look no further than the Chesapeake Country Scenic Byway. This picturesque route winds through Maryland’s Eastern Shore, tracing the stories of the Chesapeake Bay while offering travelers a front-row seat to the region’s natural splendor and historic treasures. Whether you’re a history buff, foodie, or nature lover, this drive has something for everyone — and it all leads to one perfect destination: Rock Hall.
About the Chesapeake Country Scenic Byway
The Chesapeake Country Scenic Byway stretches for over 400 miles, connecting charming towns, historic landmarks, and miles of shoreline. You can begin your journey in Chesapeake City, a canal town known for its 19th-century architecture and waterfront dining. Continue south to Chestertown, a colonial gem with cobblestone streets, art galleries, and Saturday farmers markets. Stop at the RiverArts Gallery or take a walk along the Chester River waterfront before heading to your final — and most memorable — stop: Rock Hall.
Why Rock Hall Is the Road Trip’s Crown Jewel
Tucked along the eastern edge of the Chesapeake Bay, Rock Hall is a quaint waterfront town that embodies everything travelers love about Maryland’s Eastern Shore. With its working marinas, seafood restaurants, and welcoming community, it’s the ideal place to relax, unwind, and enjoy the bay lifestyle.
Rock Hall is known as the “Pearl of the Chesapeake” for good reason. Spend your day biking around town, birdwatching at Eastern Neck National Wildlife Refuge, or soaking in the sunset at Ferry Park. Stroll the harbor or take a sailing charter to truly connect with the water. The town may be small, but it’s brimming with heart — and it offers all the charm you want from a coastal getaway.
Osprey Point: Well-Appointed Accommodations in Rock Hall, MD
To make your road trip along the Chesapeake Country Scenic Byway truly unforgettable, plan your stay at Osprey Point. Located in the heart of Rock Hall, Osprey Point offers three elegant lodging options, two full-service marinas, and a fine dining restaurant — all set against a serene waterfront backdrop. Whether you’re docking your boat, indulging in a romantic dinner, or relaxing in one of the beautifully appointed rooms, you’ll find that Osprey Point is more than just a place to stay — it’s part of the Chesapeake experience.
Ready to hit the road? Plan your Chesapeake Bay adventure and book your stay at Osprey Point’s accommodations online or by calling 410-639-2194.