There was a trading post on this spot at the head of navigation on the Appomattox River before 1850. When Peter Jones became proprietor the small settlement became known as Peter’s Point. Petersburg was granted a charter in 1748 and by the time of the American Revolution the town was important enough to be raided by British forces under the direction of turncoat Benedict Arnold.

In the early 1800s Petersburg was the rival and even the superior to its neighbor to the north, Richmond. Crippling fires in 1815 and 1826 impeded progress but in 1850, when the town was consolidated with the nearby settlements of Blandford, Pocahontas, and Ravenscroft to become a city it was the third largest in Virginia with a population of 14,010.

During the Civil War, Ulysses S. Grant based his assault on the Confederate capital in Richmond on severing the supply line from the south at Petersburg. In June of 1864 the city became the “last ditch of the Confederacy.” Four days of sharp fighting pushed the Southern lines back one mile, where both armies entrenched. The longest siege ever to take place on American soil was about to begin.

Almost immediately the 48th Regiment of Pennsylvania Volunteers, comprised mostly of coal miners, began digging a 511-foot mine shaft into the Confederate line, quietly carrying out tons of soil in cracker boxes. On July 30, after a month of digging, the Federals exploded four tons of powder under the Confederate battery, blowing 278 Southern defenders into the air. In the confusion that followed, the Union troops storming the line plunged directly into the massive crater created by the explosion rather than advancing around it. The Confederates were able to seal their defensive line and inflicted horrible casualties in a determined counterattack. The siege was to last nine months. Before it ended on April 2, 1865, a total of 42,000 Union and 28,000 Confederate troops were killed or captured in the Petersburg campaign.

The city began anew almost immediately after the war ended. The port of Petersburg was a commercial center and the city evolved into an important railroad hub as well. Census reports in 1880 indicated there were 70 more businesses operating in Petersburg than there were twenty years earlier when the Civil War began. Most found work in the tobacco factories but there was peanut processing and flour mills a silk mill, pencil plants and furniture-building as well.

Our walking tour will start where Peter Jones managed the loading and unloading of packets 350 years ago and continue up the hill to the historic Courthouse District...

1.
Union Station
River Street at Third Street

The Norfolk and Western Railway constructed this Colonial Revival passenger depot in 1909-1910 to replace an earlier structure that was damaged by rampaging Appomattox River flood waters. The Atlantic Coast Line Railroad also used Union Station for a time; the ACL’s line curved off to the northeast while the Norfolk and Western’s ran east-west. It remained an active station until 1971. 

WITH YOUR BACK TO UNION STATION, TURN RIGHT AND WALK UNDER THE ROUTE 1 OVERPASS. 

2.
South Street Station
River Street at Market Square

This original South Side Railroad station, the oldest such building in the state, was built around 1854 when the line was completed from Petersburg westward to Lynchburg, a distance of 123 miles. During the Civil War, many Confederate troops were brought here from distant battlefields and camps, and sent to the numerous Petersburg hospitals. In the final year of the war, the railroad would be the target of at least three Federal cavalry raids, with service being disrupted from time to time while the tracks were repaired. Damage from a 30-pound artillery shell can still be seen in the western freight wing where it crashed into a roof support beam. This building served as the post-war offices for the Atlantic, Mississippi & Ohio Railroad under former Confederate General William Mahone. His office was on the upper floor front window of the passenger station. This rail line is now the Norfolk-Southern. 

WALK INTO MARKET SQUARE.

3.
Old Towne Market
9 East Old Street in Market Square

This octagonal red brick building was constructed in 1879, replacing a simple frame market building. The site for a public market was donated in 1805 by Colonel Robert Bolling. In its early days it was the only place in town to buy meats and vegetables for the dinner table.

WALK TO THE EAST SIDE OF MARKET SQUARE, ON COCKADE ALLEY.

4. 
McIlwaine House
425 Cockade Alley at Old Street

This Federal-style frame residence was built around 1794 by Erasmus Gill and was later owned by George H. Jones, Mayor of Petersburg, in 1815-16.  It takes its name from Archibald Graham McIlwaine, a Petersburg industrialist and financier, who made it his residence from 1831-78. After standing vacant for nearly four decades the house, filled with exquisite woodwork buried under some 20 costs of paint, is being restored. 

TURN RIGHT AND WALK SOUTH UP THE RISE TO THE END OF COCKADE ALLEY AT BOLLINGBROOK STREET. TURN RIGHT.

5.
Farmers’ Bank
19 Bollingbrook Street  

This early Federal-style commercial building was constructed in 1817 and is one of Virginia’s oldest bank buildings. Granite string courses divide the three stories. The keystones over the windows are granite as well. As it approaches its bicentennial the building is doing duty as the Olde Towne Visitor Center. 

TURN RIGHT ON SYCAMORE STREET. TURN LEFT ON OLD STREET.

6.
Appomattox Iron Works
20-28 Old Street

This Federal style brick building was constructed between 1810 and 1825 for ironworking craftsmen. From 1899 to 1972 this was the home of the Appomattox Iron Works. The building was scheduled to be razed but escaped its date with the wrecking ball only to be torn into by a tornado in 1993. Still, the building survived to receive renovation early in this century. 

7.
Dunlop Tobacco Factory
45-127 Old Street and Market Street 

After the Civil War the economy of Petersburg recovered on the back of tobacco. In 1880 nearly seven of every ten workers in town were employed in one of the 12 tobacco factories in the city. In 1888 David Dunlop, a local magnate, constructed this expansive brick factory. Shortly it was employing over 700 people and churning out more than two million pounds of tobacco products each year. The city’s last remaining tobacco manufacturing company in Petersburg closed its headquarters in 2010; this old factory was redeveloped into living space. 

8.
Golden Ball Tavern
West Old Street and North Market Street

Here stood a dwelling house, constructed about 1764 by prosperous tobacco merchant, Richard Hanson, who, as a fervent Loyalist, fled Virginia in 1776. From the time of its erection until 1825, its sign of a large golden ball as famous in Virginia. According to tradition, British officers serving under Cornwallis were quartered here in 1781. When Petersburg was incorporated as a town in 1784, the town council and the courts used the tavern as their first meeting place. The structure was enlarged by 1820 and utilized as a hotel until after the Civil War when it was used for a number of retail ventures. The building was demolished in 1944. 

TURN LEFT ON MARKET STREET. TURN LEFT ON BANK STREET.

9.
CharlesLeonardHardwareCompanyBuilding
20-22 West Bank Street

Charles Leonard began his business in Petersburg in the 19th century as a “Manufacturer and Wholesale and Retail Dealer in Hardware, Carriage Material, Leather and Rubber Belting, Saw Mill and Ship Chandler’s Supplies,Sash, Doors and blinds, Sportsmen’s and Fishermen’s Supplies and Household Sewing machines.”  The firm moved into this four-story brick building in 1919. Look up over the altered ground floor to see the decorative brickwork on pilasters and spandrels. The building dates to 1845 and was struck by Union artillery shells during the Civil War.

10.
The Siege Museum
15 West Bank Street

The ten-month Union siege of Petersburg was the longest such military operation ever conducted on American soil. The museum portrays the human story of the Civil War's lavish lifestyles gave way to a bitter struggle for survival. The museum itself is housed in the historic Greek Revival Exchange Building, built between 1839 and 1841 as a commodities market. 

RETRACE YOUR STEPS TO MARKET STREET AND TURN LEFT.

11.
Trapezium House
244 North Market Street

Charles O’Hara was known around town for his eccentricity. When he built this three-story red brick house in 1817 he made sure there were no right angles or parallel walls because his West Indian servant told him that such a house could not harbor evil spirits. For years the place was known as “Rat Castle” because of the rats O’Hara kept as pets. 

TURN LEFT ON WEST TABB STREET.

12.
City Hall
135 North Union Street at West Tabb Street

Now serving as the Petersburg City Hall, this superb example of mid-19th century Italian Renaissance architecture began life as a United States Customs House and Post Office. The Petersburg granite-faced building is one of a series of Customs Houses designed by Ammi B. Young, Supervising Architect of the U.S. Treasury Department. Two others were constructed in Richmond and Norfolk. During the Civil War, this upper story served as headquarters for the Confederate military department of Southern Virginia and North Carolina, commanded variously by James Longstreet, D.H. Hill, George E. Pickett, and P.G.T. Beauregard. The three southern bays of the building were added between 1908 and 1910. The post office moved to Franklin Street in 1936 and the property transitioned to the city and became City Hall in 1938. 

13.
Tabb Street Presbyterian Church
21 West Tabb Street 

The Tabb Street Presbyterian Church is a monumental temple-form structure of stuccoed brick with granite detailing. It was brought to the Petersburg streetscape in 1843 by architect Thomas U. Walter in the days before he would re-design the United States Capitol dome in Washington, D.C. The building is dominated by six fluted Doric columns supporting a full entablature. It originally sported a tapered, octagonal steeple but it was removed in 1938. This is the third building to serve the congregation since its creation in 1813.

TURN RIGHT ON SYCAMORE STREET, STAYING ON THE WEST (YOUR RIGHT) SIDE OF THE STREET. 

14.
Petersburg Savings and Insurance Company
150 North Sycamore and West Tabb streets

The Petersburg Savings and Insurance Company began business June 1, 1860. It transacted a banking and insurance business, the former being much the more important branch. The company occupied this corner Neoclassical headquarters, constructed of brick on an ashlar foundation, in the late 1880s. The bricks on both the Tabb Street and North Sycamore Street facades form Ionic pilasters on the second floor.

15.
Virginia National Bank
144 North Sycamore Street

The bank was established on March 22, 1905 and moved into this Neoclassical mid-block vault in 1911. The building of limestone blocks is notable for its colossal fluted Corinthian columns rising to a triangular denticulated pediment.

WALK ACROSS THE STREET AND TURN LEFT, WALKING A FEW STEPS BACK TO EAST TABB STREET.

16.
The National Bank
147 North Sycamore and East Tabb streets 

The National Bank of Petersburg organized in 1886. This brick vault with limestone facing created in the Neoclassical style was built in 1906 for the National Bank. With its prominent Doric portico, the National is considered architecturally the finest of the three turn-of-the 20th century banks that were located at the corner of Sycamore and Tabb streets.

17.
Petersburg Courthouse
Courthouse Square
150 North Sycamore Street 

Sited on a hill overlooking downtown, the courthouse was constructed between 1838 and 1840 in the fashion of the Tower of the Winds, an octagonal marble clocktower on the Roman agora in Athens, Greece. The first story features a bell, Corinthian columns, round-arched arcade, and entablature; the second story of the tower highlights the Ionic order, with an octagonal lantern and entablature;  the top of the tower has large clock with four faces. It was designed by New York architect Calvin Pollard as the city’s Husting’s Courthouse. The term “hustings” derives from a British form of court system loosely in place in Virginia today and refers to a public space where political campaign speeches are made. The Courthouse was the official Confederate headquarters during the Siege of Petersburg.  The clock tower was a favorite target of Union cannons - an estimated 20,000 shells rained on the city during the Siege. When Petersburg fell on April 3, 1865 a Union flag was installed on the tower.

WALK UP INTO COURTHOUSE SQUARE AND AROUND THE COURTHOUSE TO ADAMS STREET. TURN LEFT ON ADAMS STREET AND RIGHT ON HENRY STREET. WALK UP INTO CENTRE HILL.

18.
Centre Hill
1 Centre Hill Court

Colonel Robert Bolling was a wealthy early American settler, merchant and planter. He is the ancestor of many prominent individuals including Presidents George H. W. Bush and George W. Bush. Robert Bolling IV built this opulent mansion in 1823 in the late Federal style. The Greek Revival style porch with Ionic columns was added during an extensive remodeling by Robert Buckner Bolling in the 1840s. A tunnel was carved from the house through the hill out to Henry Street. Since the late 19th century, when the ghosts of Civil War soldiers were first heard in the mansion, January 24th has been the night of “ghostly activity” at Centre Hill, now a house museum.

WALK BACK DOWN CENTRE HILL TO HENRY STREET AND WALK ONTO THIRD STREET THAT LEADS BACK DOWN TO OLDE TOWNE. FOLLOW THIRD STREET BACK TO RIVER STREET AND THE TOUR STARTING POINT AT UNION STATION.