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Tilghman Island and Claiborne: Maryland's Eastern Shore

From popular tourist attractions to lesser-known areas, Dolores shares destinations in Maryland as well as regional day trips.

All about the quaint towns on the eastern shore of Maryland.

All about the quaint towns on the eastern shore of Maryland.

Eastern Shore Maryland

Not far from Easton, on Maryland's Eastern Shore, Tilghman Island and Claiborne are like time capsules of the past. These Chesapeake Bay communities retain their old-fashioned charm and the peaceful lifestyle of yesteryear. Just west of St. Michaels, Maryland, these towns can be reached by traveling west on Route 33.

Do not expect much when you visit these quaint towns. You’ll find the ambiance of days gone by, terrific water views, a glimpse of life in the land of pleasant living, and not much else. The lack of traffic and level roads are perfect for cycling. When driving down these pleasant back roads, remember to slow down for bicyclists and people who stroll down the middle of the road.

There are plenty of spots for birdwatching, fishing, and crabbing, and the sunsets over the Chesapeake Bay are incredible.

Tilghman Island

On the western edge of Route 33 on Maryland's Eastern Shore, out past St. Michaels, lays Tilghman Island. Across the drawbridge, you can find a place mostly untouched by the modern world- an island filled with beautiful old homes, farms, and boats. On Tilghman Island, you can imagine a Chesapeake Bay community as it once was- peaceful, quiet, and serene.

Tilghman Island History

Fossils have shown that in prehistoric times, Tilghman Island was inhabited by giant beavers the size of bears.

Indigenous Americans lived there during the Ice Age where they dined on seafood. The area is still famous for fishing, and for crabs and oysters.

Once known as Great Choptank Island, then Foster's Island, the area was sold to the Tilghman Family in 1752. The community was established when the Tilghman Family sold off parcels of land for development in the 1840s.

Tilghman Island became populated by watermen and farmers as well as some ship-building businesses. The onset of steamboats in the 1890s created a seafood trade with Baltimore. Steamboats brought tourists over from Baltimore to escape the hot, urban summers

(photo by Dolores Monet)

Tilghman Island Today

With a population of little over 800, Tilghman Island is still home to farmers and watermen. Charter boats take visitors out fishing on the Chesapeake Bay for striped bass (rockfish), trout, spot, and croakers. Several marinas offer berths as well as boat rentals for tourists and visitors.

Black Walnut Point, at the tip of Tilghman Island, features an excellent view of the Chesapeake Bay. It is a great place to fish, cycle, or go birdwatching for eagles, osprey, herons, sandpipers, terns, and hawks.

Old Town America - Tilghman Island

Old Town America - Tilghman Island

On a recent trip to Tilghman Island, I spotted several old homes with interesting architecture.

Houses often feature a W shape on the front of the house, which is unique and attractive, and must be great for catching the breeze on a hot summer day and bringing in light during the cooler months.

Claiborne (photo by Dolores Monet)

Claiborne (photo by Dolores Monet)


Claiborne is a quiet village just off Route 33, home to 147 souls, a public boat ramp, and a tiny, hidden beach. Claiborne retains an old-fashioned charm with tree-lined streets and an ambiance that can make you feel like you're on a movie set for a film set in the old south.

Claiborne History

After coming to North America in 1621, William Claiborne, a member of the Virginia council, established a trading post on nearby Kent Island. A tobacco farmer, Claiborne also entered into the fur trade with the Susquehannock Indians. He was the first European settler in Maryland.

When Leonard Calvert, the first Governor of Maryland attempted to claim the territory for Maryland, Claiborne refused to give up his rights. The fight that followed proved to be the first naval battle fought in North America.

Claiborne then traveled to England to petition the king, but the king said the claim belonged to Maryland.

In the mid-1800s, Bingham's Steamboat Wharf provided dockage for an oyster company. The small town had a general store and a few watermen's homes.

In 1886, the Baltimore and Eastern Railroad began ferry service between Claiborne and Bay Ridge on the western shore of the Chesapeake Bay. Hopes of making Claiborne a tourist destination (thankfully) failed but the railroad transported people to Easton and Ocean City. The railroad company failed in 1927, leaving Claiborne to the watermen. Remnants of the ferry dock can be seen there today.

Claiborne Today

Claiborne today remains a simple community of a few homes.

On a recent visit to Claiborne, we spent an evening eating steamed crabs and walking to the boat ramp to watch the sunset over the Chesapeake Bay. We then sat out on the porch of an old waterman's home to listen to the sigh of a breeze stir through the cornfield across the street and two Great Horned Owls call to each other in the trees. The evening could not have been more beautiful.

(photo by Dolores Monet)

(photo by Dolores Monet)

(photo by Dolores Monet)

(photo by Dolores Monet)