A lively mix of historic homes, taverns, restaurants, and shops, Alexandria seems to exist in two or three centuries at once. Founded in 1749 by Scottish merchants eager to capitalize on the booming tobacco trade, Alexandria first emerged as one of the most important ports in Colonial America. The city dwarfed Georgetown—Washington's oldest neighborhood—in the days before the Revolution, and until the Civil War had one of the country's largest slave markets. Alexandria is linked to many significant events and personages of the Colonial, Revolutionary, and Civil War periods. George Washington had a town house and attended church here, though he lived a few miles south in Mount Vernon, and members of the Lee family of Revolutionary and Civil War fame lived here as well.

For many African-Americans fleeing slavery, part of their journey on the Underground Railroad included a stop in Alexandria. This was true of one of the largest and most celebrated slave escapes, in which 77 individuals, many of whom labored in homes in Alexandria, took refuge on the Pearl, a ship bound for New Jersey, which left from Washington's 7th Street Wharf in April 1848. Unfortunately the ship was captured in Maryland and most of its passengers were returned to Bruin's Slave Jail. Harriett Beecher Stowe modeled her account of the slave trade in Uncle Tom's Cabin on this establishment.

This vibrant past remains alive in the historic district of Old Town Alexandria—an area of cobbled streets, restored 18th- and 19th-century homes, churches, and taverns close to the water. The main arteries of this district are Washington Street (the G. W. Parkway as it passes through town) and King Street. Most points of interest are on the east (Potomac) side of Washington Street.

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