Tilghman Island was admitted to Talbot County in 1707. Originally called the "Great Choptank Island", it was known also as Foster's Island, and later Ward's Island. In the mid-1700s the island was inherited by Matthew Tilghman who changed the name to Tilghman Island. During the mid-1800s General Tench Tilghman bought the body of land and established two steam sawmills. In the early 19th century, parcels of land were sold to oystermen wanting to close proximity to the prime harvesting grounds surrounding Tilghman Island. By the turn of the century, two thriving industries - steamboat service and the seafood had been established. The island later became a popular vacation haven for vacationers, who were anxious to experience the well-known fishing and accommodations. The mainland at Knapps Narrows features the drawbridge which continues to serve as the mainland connection to Tilghman Island. Maps dating back as far as the late 1600s reflect the existence of a bridge connecting these two villages.
The Methodist Church was built in 1784 and the current church on the main road was built in 1879. St. John's Chapel , circa 1891 has been restored and is now available to all denominations for weddings and christenings alike. In the early days circuit riders would arrive by horseback to deliver sermons at the church.
A distinctive house style (circa 1890) which is known as a "V" shape, has three gables on the front and has become a Tilghman classic. Many houses of this style were built on the island but only a few have survived. Surrounded by the famous Chesapeake Bay and the Choptank River, most residents have earned their livelihood from the bounty of the Bay. Crabbing, oystering, tonging and dredging, seafood packing and canning has provided employment opportunities for islanders. Boat building was a natural and the two of the most popular models - the skipjack and log canoe were built on the island. Today, the largest fleet of working skipjacks graces the waters of Dogwood Harbor.
Approximately 970 people reside on the island. Fine dining, award-winning accommodations and restaurants keep vacationers returning. Kayaking, sailing, skipjack charters, sport fishing, bicycling, bird watching and simply relaxing are the among the favorite things visitors enjoy. Every year during August, thousands of Monarch butterflies find the island as the perfect resting place as they travel back to Mexico for wintering.