Take a trip straight to the source of the Chesapeake's charms - and don't forget to bring your appetite for fresh seafood.
Home to immaculately preserved waterfront towns and mansions, the upper Chesapeake Bay has a rich maritime traditional all its own. Begin your tour in Havre de Grace, at the junction of the Susquehanna River and the Bay, with the Steppingstone Museum, the Susquehanna Museum of Havre de Grace, and the Havre de Grace Decoy Museum. Don't leave without visiting one of the East Coast's oldest operating lighthouses at Concord Point.
After you cross the Susquehanna, you'll see the mammoth Conowingo Hydroelectric Plant and Dam, where the mighty river is harnessed to create electric power for the entire region. The nearby town of North East, settled in 1700, offers options for a late lunch, several antique shops, and the Upper Bay Museum, with its engaging collection of nautical and historical artifacts, some of which come from the region's Native American inhabitants.
Heading south, you'll come upon Chesapeake City, a collection of 19th-century houses, inns, restaurants, and stores divided down the middle by the Chesapeake and Delaware Canal. Here, you might just see a towering ocean freighter passing under the town's high-arching bridge. The last stop in your busy day is colonial Chestertown. Check into a small inn or quaint bed and breakfast, then head out to dinner or take a sunset walking tour.
The next morning, you'll awaken to a beautiful enclave of riverside mansions and shaded streets draped with ancient trees. Chestertown is home to Washington College, the only college to which President George Washington lent his name. If you wish, you can learn more about the local history at the Geddes-Piper House.
Next, stop in Denton, a small town on the Choptank River in Caroline County, and visit the Museum of Rural Life. The ride through nearby Queen Anne's County is dotted with small, historic towns like Queenstown, Kent Island, Church Hill and Centreville.
As you work your way down the Eastern Shore, you'll come upon two more towns, these the most celebrated on the peninsula: Easton and St. Michaels. First take a look around Easton, established in 1710. Walking tours highlight the many different architectural styles employed in its historic homes. You can also tour the Academy of the Arts' extensive collections of 19th- and 20th-century works, and, after dinner, you might consider attending a concert at the Avalon Theatre, a recently restored 1921 art deco showplace.
Complete your tour at the aforementioned postcard-pretty town of St. Michaels, which grew around an Episcopal parish founded in 1677. Spend the day walking among the Colonial and Victorian homes and visiting the shops, inns, and restaurants that line the narrow main streets, wooden walkways, and piers.
The Chesapeake Bay Maritime Museum on the harbor has a working boatyard that boasts the world's largest collection of historic Chesapeake Bay boats. It's also where the Hooper Strait Lighthouse stands. To cap off your journey, head out to the timeless town of Tilghman Island for a regional dinner and a grand sunset on the water.