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12 Historic Squares of High Street

History of High Street
Portsmouth was founded as a town in 1752, on 65 acres of land on the shores of the Elizabeth River. The town was founded byPortsmouth-Virginia-riverfront William Crawford, a wealthy merchant and ship owner who at various times had held office as the Norfolk County presiding court judge, high sheriff, militia lieutenant colonel, and representative to the House of Burgesses. Because of his militia service, he is frequently referred to as “Colonel Crawford.” The 65 acres were part of Colonel Crawford’s extensive plantation and were constituted as a town by an enabling act of the General Assembly of Virginia.

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. The town was 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 Colonial America.
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.

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Still standing is the original downtown intersection that the city’s founder, Col. William Crawford, dedicated to public use — with 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 a history lover’s paradise.

High Street Highlights
If you head west on High Street, you’ll find shops, restaurants, and museums. The Children’s Museum of Virginia and the Virginia Sports Hall of Fame face each other on opposite sides of High Street, offering fun exhibits and interactive activities for people of all ages.

At 421 High Street, you’ll find the Commodore Theatre. Listed on the National Register of Historic Places and VirginiaCommodore_Theatre_Portsmouth_VA Landmarks Register, it was at the time considered the best-equipped theater in Hampton Roads. Today, the Commodore is a luxuriously restored 1945 Art Deco style motion picture theatre presenting first run films with a fine dining restaurant within the main auditorium.
After checking out the theater, head back east on High Street to the corner of Court Street and High Street, where the city’s founder created a town square. In the original layout for Portsmouth, these four corners were designated for a church, a market, a courthouse and a jail.
On the northwest corner, you’ll see an imposing Greek Revival building, surrounded by a wrought-iron fence and nearly hidden behind the massive oak trees that shade its courtyard. Built in 1846, it served as the Norfolk County Courthouse until 1960. Now it is home to the Courthouse Galleries, an art museum with two spacious galleries of ever-changing exhibits. From the original hand-colored lithographs of John James Audubon to the 17th-century engravings that depict some of the earliest images of Virginia Indians, the Courthouse Galleries museum continually strives to promote a greater appreciation and understanding of the arts.

A Tour of the 12 Merchant Squares of Historic High Street
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Bloomsberry Square– bounded by Crawford, King, Middle and High Streets- named for Bloomsbury, a district of London, England.

Market Square– bounded by Middle, King, Court and High Streets. In 1752 when Colonel William Crawford established the town of Portsmouth he designated part of this square for a market, hence the name, although a market was never erected at this location.

Church Square– bounded by Court, king, Dinwiddie and High Streets. When William Crawford, founder of Portsmouth, laid out the street plan in 1752, he designated the intersection of High Street and Court Street as the town center and set aside space for a parish church. In 1761, when the Vestry of Trinity Church was formed with Crawford as a member, the original church building comprised most of what is now the nave.

Dinwiddie Square– bounded by Dinwiddie, King, Washington and High street. It was named for Robert Dinwiddie (1693-1770), lieutenant-governor of Virginia, 1751-1758.

Cheshire Square– bounded by Washington, King, Green and High Streets. It was probably named for the English County of Cheshire.

Montgomery Square– bounded by Green, King, Effingham and High Streets. It may have been named after Robert Montgomery (1736-1775), brigadier general in Continental Army who was killed leading the assault on Quebec, or it may have been named after the Herbert family, hereditary Earls of Montgomery.

Heading East from Effingham Street on High Street towards the river.

Washington Square– bounded by Green, High, Effingham and Queen Streets. It was named after George Washington (1732-1799), commander–in-chief of Virginia troops, 1775, and of all Continental troops, 1775, first President of the United States.

Anderson_Wright_olde-towne-portsmouthDevonshire Square- bounded by Washington, High, Green and Queen Streets. Named after the English County of Devonshire.

Oxford Square- bounded by Dinwiddie, High, Washington and Queen Streets. Named after the well known street in London, England.

Prison Square- bounded by Court, High, Dinwiddie, and Queen Streets. It was so named because Crawford in 1752 had designed part of this square for the erection of a prison.

Courthouse Square- bounded by Middle, High, Court and Queen Streets. Crawford designated part of this same square for the erection of a court house, hence the name Court House Square.

Golden Square– bounded by Crawford, High, Middle and Queen Streets.

Whether coming to visit or an afternoon or an extended stay, historic Olde Towne Portsmouth offers a break from the ordinary. Olde Towne offers superb shopping and exquisite dining along the High Street corridor that makes up the 12 historic squares laid out in 1752 by Col. William Crawford, the city’s founder. Visit Olde Towne’s fine antique shops, remarkable specialty stores and sophisticated art galleries. Dine in Portsmouth’s exceptional selection of fine restaurants, cafes, bistros and pubs for a delectable experience. The merchants and restaurant here in Olde Towne are committed to making your visit as memorable as it is rewarding, showing your that the heart of our quaint historic seaport is based on the enduring distinction of fine customer service.

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