The United States Census Bureau reports that the island has 31.62 square miles (81.90 km2) of land area.

In 1850, the town of Stevensville, was founded after the sale of farms owned by James and Charles Stevens and prospered as a major hub for steamboat travel across the Chesapeake Bay.

Also during this time, small resorts on the shores of the Chesapeake Bay and the Atlantic Ocean were established in the area.

Farming returned to the economy in the nineteenth and twentieth centuries with farmers growing crops including corn, wheat, berries, and melons.

Many of the island's inhabitants worked as watermen in the expanding seafood industry capitalizing on the Chesapeake's supply of Maryland Blue Crab, rockfish, and oysters.

In 1952 the Chesapeake Bay Bridge was completed, connecting the island directly to the Baltimore-Washington Metropolitan Area.

The bridge completely replaced the steamboat system and also led to further growth of Kent Island and the rest of the Eastern Shore.

In 1973, to accommodate growing traffic across the bay, the bridge was expanded with an additional span built next to the existing one.

In September 2003, Kent Island was one of the many places in the Chesapeake Bay Area affected by Hurricane Isabel.

Today, Kent Island is considered a suburb of the Baltimore-Washington Metropolitan Area and was home to 16,812 residents at the time of the 2000 U.S. Census.

Several buildings on the island that are still leftover from the 19th century and earlier include the Cray House, a rare remaining example of post and plank construction, the old Stevensville post office (left, yellow building in center), the Stoopley Gibson Manor, Christ Episcopal Church, and the Stevensville Train Depot (right).

The bridges that currently connect Kent Island to the mainland, or once did, are as follows: Access to Annapolis is available via MTA Commuter Bus Service Route 210.

Before the construction of the Bay Bridge, ferry services connected the island directly to Baltimore, Annapolis, and the small peninsula on which St. Michaels, is located.

Into the 1930s the Baltimore and Eastern Railroad operated passenger service from Love Point on the northern extreme of the island east to Queenstown, Easton, Hurlock, as well as Salisbury's Union Station, Ocean City, Maryland, Berlin, and Delmar, Delaware.