Take a trip straight to the source of the Chesapeake's charms - and don't forget to bring your appetite for fresh seafood.
Day 1
The upper Chesapeake Bay is home to immaculately preserved waterfront towns and mansions, and a rich maritime tradition all its own. Founded at the junction of the Susquehanna River and the Bay, Havre de Grace offers a glimpse of the past at the Steppingstone Museum and the Susquehanna Museum of Havre de Grace, and a vast collection of carved waterfowl at 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, stop at the mammoth Conowingo Hydroelectric Plant and Dam, where the mighty Susquehanna is harnessed to create electric power for the region. The nearby town of North East, settled back in 1700, offers several restaurants and antiques shops, along with the Upper Bay Museum and its engaging collection of nautical and historical artifacts dating back to the region's Native American inhabitants.
Heading south, you'll come upon Chesapeake City, a collection of 19th-century houses, inns, restaurants and shops divided down the middle by the Chesapeake and Delaware Canal . 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 a sunset walking tour.
Day 2
When the sun rises, you'll awaken to a beautiful enclave of well-preserved riverside mansions and shaded streets draped with tall, aged trees. Chestertown is home to Washington College, the only college to which President George Washington lent his name. You can learn about local history at the Geddes-Piper House.
Next, stop in the small town of Denton, 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. Stop along the way for a snack or to visit a little museum.
As you work your way down the Eastern Shore, you'll come upon two of the peninsula's most celebrated towns, both in Talbot County. First comes Easton, established in 1710. Walking tours highlight the many different architectural styles employed in its historic homes. You can tour the Academy of the Arts' extensive collections of 19th- and 20th-century works and then, after dinner, take in a concert at the Avalon Theatre, a recently restored 1921 art deco showplace.
Day 3
Complete your tour at the 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 and the wooden walkways and piers that hug the water.
The Chesapeake Bay Maritime Museum on the harbor has a working boatyard that's home port to the world's largest collection of historic Chesapeake Bay boats. It's also where the Hooper Strait Lighthouse stands. Head out to the timeless waterman's town of Tilghman Island for a waterside dinner and a grand sunset over the Bay.
