Olde Towne, also spelled Old Town, though only the wacky fencers use "Olde Town", is situated in the eastern and southeastern area of the city along the Potomac River. It was originally laid out in 1749, making it the oldest section of the City and is a historic district.[21] Olde Towne is chiefly known for its historic town houses, art galleries, antique shops, and restaurants.

Some of the historic landmarks in Old Town include General Robert E. Lee's boyhood home, the Lee-Fendall House, a replica of George Washington's townhouse, Gadsby's Tavern, the Stabler-Leadbeater Apothecary Shop, and the Torpedo Factory art studio complex (see the "Recreation" paragraph below). River cruise boats and street entertainers frequent the large plaza at the foot of King Street; the Mount Vernon Trail also passes through. Old Town is laid out on a grid plan of substantially square blocks. The opening of the Washington Metro King Street station in 1983 led to a spurt of new hotel and office building development in western Old Town, and gentrification of townhouse areas west of Washington Street which were previously an African-American community.

Market Square in Old Town is believed to be one of the oldest continuously operating marketplaces in the United States, (from 1753 until present day),[22] and was once the site of the second-largest slave market in the U.S. Today it contains a large fountain and extensive landscaping, as well as a farmers' market each Saturday morning.

In the center of the intersection of Washington and Prince streets stands a statue of a lone Confederate soldier which marks the spot where CSA units from Alexandria left to join the Confederate Army at the beginning of the American Civil War.[23] The piece is entitled Appomattox and was cast by M. Casper Buberl in 1889.[23]