Olde Towne Portsmouth features a scenic waterfront, upscale dining, a plethora of antique and boutique shops, and the largest collection of historic homes between Olde Towne Alexandria, Va., and Charleston, S.C. The area north of High Street has been listed as the Olde Towne Historic District and is mainly residential. The style of the buildings vary by time period, with many Federal and Greek Revival houses located south and just north of High Street. As the turn of the 20th century, the Revival styles, such as Classical Renaissance, Gothic and Romanesque were incorporated into the construction of homes. However, it is during the Reconstruction period that Portsmouth built its grand churches, which dominate its skyline.

Still standing is the original downtown intersection that the city's founder, Col. William Crawford, dedicated to public use -- one corner each for a church, a market, a courthouse, and a jail. In fact, Trinity Episcopal Church on the southwest corner -- founded in 1762 -- still rings its bells across the street from the 1846 Courthouse that now serves as a museum.  With six districts listed on the Virginia Landmarks Register and the National Register of Historic Places, Portsmouth is rich in history.

Portsmouth's history dates to the settlement of Jamestown in 1607. Captain John Smith, while mapping lands surrounding Jamestown, sailed down the Elizabeth River and marveled at the lush beauty of the terrain.  The first settler on the land, which is now Portsmouth, was Capt. William Carver, who was issued a land grant in the mid-1600s. In 1672, Capt. Carver stabbed Thomas Gilbert and following Bacon's Rebellion in 1676, Capt. Carver was captured, recalled to England, was tried and hanged. His land was forfeited and given to Col. William Crawford in 1715. The original town was enlarged in 1763, in 1811, and in 1899.

Portsmouth gets its name from the English naval port of Portsmouth, England. The town was laid out checkerboard style with 122 half-acre lots around its town square at High and Court streets. Streets were organized in a grid pattern with street widths alternating between 32, 50 and 100 feet. Each block or square was named for noted Virginians, Englishmen, or places in England or the United States.

Streets were named similarly. High Street was named for the main commercial corridor in Portsmouth, England. It is 100 feet wide, with two narrow parallel streets of 32-foot widths (Queen and King streets), located to the north and south. Narrower streets served as alleys for High Street, facilitating the access to commercial buildings from the rear.

Because of its excellent location on the Elizabeth River, early Portsmouth was rich in waterfront commerce. The town grew from the river inland.  Col. Crawford built his home on Crawford Street, and most of the houses were built in the eastern portion of the city. In 1793 there were 300 homes and a population of 1700 people, and by 1806 there were 700 homes and 3,000 inhabitants.  A rail line was built to handle the shipping of goods to and from the wharves.

During the American Revolution, Portsmouth was spared as Norfolk burned following the defeat of Lord Dunmore at Great Bridge; however, a number of homes were set afire by the American Revolutionary War Colonel Charles Lee because he felt that many of the Portsmouth inhabitants were too sympathetic to the British cause. In 1779, Commodore Sir George Collier invaded Portsmouth, ransacked the town, and destroyed 137 vessels in the harbor. A year later, General Benedict Arnold (right) took command of the town.  He returned to New York to be with his pregnant wife, and General Cornwallis took command of the town, only to leave shortly thereafter to fight Washington and Lafayette at Yorktown.  Many believe if General Cornwallis did not go to Yorktown, the fight would have been in Portsmouth at Fort Nelson.

The War of 1812 followed after only 35 years of peace. The British were repelled at Craney Island and Olde Towne was never invaded.

Portsmouth grew as a maritime center, and in 1827 the U.S. Navy built its first hospital in Portsmouth at the revolutionary war site, Fort Nelson. In 1833, the Navy constructed the first drydock in North America at the Gosport Navy Yard, now the Naval Shipyard in Portsmouth. Both facilities are still used by the Navy.

In 1861, Virginia seceded from the United States. John Porter designed and converted the USS Merrimac into the CSS Virginia and the famous battle between the CSS Virginia and the USS Monitor, the first battle between ironclad ships, was fought just down the river at the junction of the Elizabeth and James Rivers. Pieces of the ironclad are on display at the Portsmouth Naval Shipyard Museum.  Nineteenth century Portsmouth relied heavily on shipbuilding. In 1894, the Seaboard Air Line Railroad came to town.

The first World War turned Portsmouth into a boomtown, bringing thousands of new jobs to the area due to the construction of dry docks and ships, but in 1923 the Washington Naval Limitation Treaty stopped all warship construction and the shipyard laid off 75 percent of its workforce.

World War II provided rapid economic growth for Portsmouth. In 1943, 43,000 people were employed in the shipyard. In order to house this huge influx of people, many of the large, older homes in Olde Towne were converted to apartments. After the war, the first of two tunnels opened in 1952; and the Elizabeth River passenger ferries, which had served as a major means of transportation, ended.

Olde Towne Portsmouth has survived wars, fires, plagues, depressions, and occupation by foreign troops and will continue to survive, due to the spirit of the people who call Portsmouth home.

An early building of note is the House & Commercial Building located on 300 High Street. This building dates from the late 18th century and is characterized by an elevated basement and progressively shorter stories from the first to third story. This building is the oldest building in the Olde Towne district and is significant is Portsmouth's history because it was headquarters for Benedict Arnold's occupation of Portsmouth. It has a plain façade but an elaborate Doric porch and is really not representative of Federal style architecture. It has one of the few remaining elevated basements.

Take a self-guide walking tour of Historic Olde Towne.  Go to Olde Towne Tours & Excursions.