The state of Maryland is divided in half by the Chesapeake Bay. Before the Chesapeake Bay Bridge was built in 1952, the Eastern shore was physically and socially removed from the Western Shore. While the state capital, Annapolis, and Baltimore, a shipping and industrial town are located on the Western Shore, the Eastern Shore was compromised of small towns, farms, and water oriented communities. In the late 1800's steam boats brought some tourists to the Eastern Shore to escape the heat of urban areas.
The building of the Chesapeake Bay Bridge increased tourism and historically swelled the population of that formerly removed section of Maryland. While things have changed dramatically, there are still remnants of the old fashioned charm of the Eastern Shore, much of which can be found along Route 33, just west of Easton.
Saint Michael's is just such a place. Once, a thriving ship building and waterman's' town, St. Michael's today has retained its quaint historical atmosphere. On weekends, the main street is busy with tourists, shopping at the boutiques, galleries, antique shops, and craft stores.
The Chesapeake Bay Maritime Museum, open since 1965, draws visitors interested in a peek at history. Featuring both indoor and outdoor displays, old boats, a lighthouse, and several outbuildings, the Chesapeake Maritime Museum holds festivals centered around the area's history, commerce, and fishing. In September, the museum holds its annual Mid-Atlantic Small Crafts Festival, drawing people who enjoy skiffs, canoes, and kayaks for workshops and demonstrations.
The community also draws boats with its marina, and offers boat charters for a ride on the Bay or a day of fishing.
Cyclists enjoy the area for its level roads, which, once past St. George. Michael's, are reliably quiet.
Keep traveling west on Route 33, past St. Michael's to the public boat ramp at Claiborne. You will not find much to do in Claiborne and therein lies its appeal. A small town of a very few homes, Claiborne is named for the man responsible for the first naval battle in North America. Having established himself as a tobacco farmer and trapper in the early 1600's, William Claiborne strongly opposed to being included in the new territory of Maryland, drawing the ire of Maryland's first governor, Leonard Calvert.
Route 33 ends at Tilghman's Island, an attractive water oriented community on the Chesapeake Bay. Here, you will find farms, a marina, and beautiful older homes. Do not worry about crowds on Tilghmans' Island. A slow drive along its streets is a pleasure when you see the historic homes and excellent water views. Tilghman's Island ends at Black Walnut Point, a wonderful spot for fishing, bird watching, and dramatic Chesapeake Bay sunsets.