Between 1813 and 1962, steamboats ruled the Chesapeake Bay. This was reflected in a fascinating and important era in which trade and travel were made more convenient with steamers that linked parts of Maryland and Virginia, with distant and isolated, rural communities along the Eastern Shore, in particular. Steamboats served places like Piankatank River and Occohannock Creek in Virginia, and Hudson Creek, Bushwood, and Rock Point in Maryland. It made possible access to certain goods and services typically unavailable in rural areas, along with opportunities for leisure and entertainment.

There were various types of steamboats on the Chesapeake Bay, all serving a specific function. The packet steamboats were the most common; they were medium-sized and fast, and transported passengers, freight and domestic mail. The rural areas and the city were made accessible with a large fleet of smaller vessels-steam ferries, while excursion steamers were more elaborate, colorful and beautifully decorated, and made drop-offs at popular resorts on the Bay, including Tolchester and Betterton in Kent County.

The steamer, Chesapeake, was the Bay’s first steamboat, and her first trip was made on June 13, 1813, a one-day excursion from Baltimore to Annapolis. Later, she was operated regularly from Bowley’s Wharf, Baltimore to Frenchtown on the Elk River as a transfer vessel that took passengers to stagecoaches bound for New Castle and Delaware. The Eagle, the Bay’s second passenger steamer, built in Philadelphia in 1813, became the first to make the journey between Baltimore and Norfolk in 1815.

Individual entrepreneurs were the pioneering owners of steamers during the early part of the 19th  Century, but steamboat companies became prominent operators in the Tidewater region, which included Maryland and Virginia, with roughly 20 lines operating at the time. The Weems Line, which began in Baltimore in 1819, was one of the most well-known passenger freight steamboat lines. It operated a fleet of steamers out of Baltimore and down the Chesapeake Bay, including the Surprise, Eagle, Patuxent, Mary Washington and Planter. Boasting the biggest and fastest steamers on the Chesapeake Bay was the Baltimore Steam Packet Company, nicknamed the Old Bay Line, which provided services largely between Baltimore and Norfolk.

The 1920s ushered in the waning of the steamboat era, as railroad service expanded, improvements were made on roads, and cars offered an easier and more reliable means of transportation. Additionally, the 1933 Chesapeake–Potomac hurricane further hastened the end of the steamboat era, having destroyed the majority of the steamship landings in Maryland and Virginia. The Old Bay Line was one of last to provide service on the Chesapeake Bay.