Tilghman On Chesapeake is located on Tilghman Island is the southernmost tip of Talbot County, Maryland. Surrounded by the waters of the Choptank River, Harris Creek and the Chesapeake Bay, it is truly a water lover’s paradise. It was originally charted in 1608 by Captain John Smith who called it a “most delightsome land.” The island has always been known for its bountiful harvest from the Chesapeake Bay, and it is home to the largest fleet of working skipjacks on the bay.

Oxford, Cambridge, St. Michaels and Annapolis are within a half days sail. The best fishing on the bay is only minutes away and numerous rivers, coves and inlets are nearby for enjoying water skiing, wind surfing and crabbing. Nature enthusiasts enjoy a wide variety of birds and waterfowl.

Residents of Tilghman Island live in peaceful seclusion, while remaining within easy access to other popular Eastern Shore destinations. Tilghman Island is 12 miles from the popular town of St. Michaels and 22 miles from Easton, Maryland, the colonial capital of the Eastern Shore. There are several quaint shops and four excellent restaurants offering a variety of cuisines.

''Take time out from your busy schedule ... visit Tilghman On Cheapeake today.''
Ken, Bill, Dolores, and Paul.

Tilghman Island was first charted by Captain John Smith in 1608. Since that time the island has been inhabited by those brave men and women who have pioneered the seafood business of the bountiful Chesapeake Bay. The name Tilghman Island was derived in 1775 by owner Matthew Tilghman. The island suffered a substantial loss of resources by the British in the War of 1812. In 1890 Steamboat service was established and continued well into the 20th century. Travelers were escorted by horse and ox drawn vehicles to their recreational destinations. And the island became a popular haven for vacationers who were drawn by superb fishing and genteel accommodations. The friendly folks on Tilghman Island, many of whom are descendants of centuries of island heritage, offer the same hospitality, seafood and warm friendliness that has existed here for generations. Discover our quiet lifestyle reminiscent of days gone by. Tilghman Island offers a wide array of seafood, restaurants, lodging, B&Bs, shops, sportfishing, hunting, crabbing, marinas and marine facilities.
“Great the blessing, God has given,
All around its fertile shores,
And the welcome that awaits you,
Stranger, to this home of ours--
Tilghman Island!”
by Raymond Sinclair (1954)