Visitors to the Eastern Shore usually start at Easton. Called the "Colonial Capital of the Eastern Shore," this town values its visitors. Route 50 is filled with reasonably priced chain hotels, and the downtown district has many worthy restaurants.
Since its founding in the late 1700s, St. Michaels has looked to the water for its livelihood. Shipbuilding made it famous. Log canoes were first workboats and then became better known as racing boats. Bugeyes and Baltimore clippers were built here. Watermen came to sell their catch, and canneries and oyster-packing plants sprang up. Local residents are proud of the night residents here fooled the British and saved their town during the Revolutionary War.
Today, St. Michaels is a popular destination for boaters, who are crammed into the harbor on sunny weekends. It's also bed-and-breakfast heaven; many have views of the beautiful Miles River. Make time for the Chesapeake Bay Maritime Museum, where the history of the whole Chesapeake Bay is celebrated. The town's streets also offer a variety of shops and restaurants.
Keep driving southeast on Route 33, the road from Easton to St. Michaels, for about 8 miles and you'll arrive on Tilghman Island. Cross the Knapps Narrows Bridge, and you'll find yourself miles from the bustle of the city. Though some development has filled a cornfield here and there -- especially at the waterline -- this is the place for true Eastern Shore living: ospreys to wake you in the morning, stars to light the night, skipjacks and crabbing boats bobbing in the harbor. Come for fresh seafood, quiet roads, and water views. Tilghman is a good place to spend a day with a camera or a bike, or even a kayak. Bring your fishing pole, as there are plenty of places on the island -- not to mention charter boats for hire -- to cast your line. The few hotels and B&Bs are welcoming places that help you enjoy the quiet Eastern Shore way.
Oxford is a refined place, with a shady park and beach in the center of town. It wasn't always so quiet, though. One of the state's oldest towns, it was the Eastern Shore's first port of entry in the 1700s. It was home to many of Maryland's prominent citizens, including Robert Morris, a shipping agent, and his son Robert Morris, "financier of the Revolution," and Tench Tilghman, George Washington's aide who carried the news of Cornwallis's surrender to the Continental Congress. Tilghman is remembered with a monument in Oxford Cemetery. Although Oxford is quieter than St. Michaels, the peace is a big part of its charm. There aren't many tourists, but there is a leafy park set on a narrow beach and charming old streets that are best seen at a slow pace.
You can also ride the tiny Oxford-Bellevue Ferry, one of the oldest in the country. Of course, you can take the ferry going the other way, making Oxford your destination.