Isle of Wight County

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Committees of Safety Created at the 1750 Courthouse
Beginning in 1775, local patriots under the direction of the appointed county magistrates, formed committees of safety to organize local militia units and secure supplies of powder and ball ammunition. Militia leader Josiah Parker of Macclesfield, among other notables with military and maritime experience, presided over these meetings to prepare Isle of Wight County citizens in the event Crown Forces appeared. As the current royal government court structure in the county, the 1750 Courthouse building served as the venue for these revolutionary assemblies.

Militia Musters on the Courthouse Green
Lot 33 of the original 1750 Smithfield land use plat lying directly across the street from the 1750 Courthouse was designated as the courthouse green. On monthly court days the major activity here was the assembly of purveyors of the many excess products produced on local farms. This one-acre green was also the primary assembly area for the local colonial militia when mustered. During the Revolutionary War, units came here to train in the techniques of 18th century tactical warfare.

Fort Boykin
Originally fortified in 1623, this strategic promontory on Burwells Bay was significantly reconstructed in 1776 as an extensively fortified earthwork to deter and defend against British naval incursions up the James River. Royal Navy warships never threatened the fort, named in honor of local patriot leader Francis Boykin. Refortified in 1812 for America’s “Second War of Independence,” Fort Boykin played a major role in defeating several British landings. This defensive work was again rebuilt and strengthened in 1861 to serve as a strongpoint protecting against Union Navy riverine advances toward Richmond. Following four naval gunfire assaults in May of 1862, Confederate forces were withdrawn when the position was deemed no longer necessary.

Benedict Arnold’s Campground at Pierceville
After landing at Hardy’s Ferry on Lawne’s Neck on January 14, 1781, and following skirmishes at Flowerdew Hundred and Cobham Wharf, Benedict Arnold’s army of some 800 regulars, loyalists and Hessian “Jaeger” encamped on the grounds of Pierceville, the home of one of Isle of Wight County’s most prominent landholders, Thomas Pierce.

Mackie’s Mill Skirmish
In January 1781, Benedict Arnold, in command of some 800 British regulars, loyalists and Hessian auxiliaries, appeared in the Chesapeake Bay after sailing from New York. Ordered to disrupt local patriot operations, he proceeded up the James River, burned the recently established capital in Richmond and returned down the river, moving overland to secure the port of Portsmouth. Debarking his small army north of Smithfield on the 15th of January, Arnold encamped on the edge of town. Early the next day he continued his march toward Portsmouth. His right flank element encountered the 200-strong Isle of Wight Militia force under Colonel Josiah Parker at the site of Mackie’s Mill. Resistance by the militia caused Arnold to employ his German riflemen against Parker’s two small cannon crews with devastating effect. Suffering unacceptable casualties, Parker ordered a withdrawal by his greatly outnumbered forces. Arnold continued his advance, capturing several Isle of Wight County Militia soldiers. Despite the brave delay tactics of local militia, Benedict Arnold achieved his objective of occupying Portsmouth. His army reembarked and returned to New York.

Captain Pierce Captured Near Wrenn’s Mill
According to the journal of Hessian Captain Johannes Ewald, the owner of Pierceville was captured near Wrenn’s Mill on January 15, 1781. Militia Major Thomas Pierce of Pierceville was reconnoitering alone the approach of Benedict Arnold’s invading force when he was captured by one of Ewald’s riflemen. This lucky Hessian auxiliary soldier, under military protocols, became the beneficiary of the “booty” of 1,000 pds. paper money, a fine gold watch and a beautiful horse.

Arnold’s Regiment Crosses Red Point Bridge
On the morning of January 16, 1781, Benedict Arnold sent his 200 strong 80th Regiment of foot soldiers across wooden Red Point Bridge to engage reported patriot militia units along the Pagan River. They continued along the east shore of Cypress Creek to threaten Colonel Josiah Parker’s Isle of Wight County Militia who were blocking Arnold’s planned route to Portsmouth. This small bridge at the east foot of Water Street (now South Church Street) was the only access to the Red Point area on the other side of Cypress Creek and areas east of the new (1750) Town of Smithfield.

John Sinclair House
At 335 South Church Street in Smithfield stands the home of local Revolutionary War patriot and notable privateer John Sinclair. Using letters of marque and reprisal, he waylaid and captured many English ships bound for the colonies to resupply his majesty’s forces. He is noted for carrying much needed ammunition to the American Army and piloting the French Fleet through the capes into the York River. This site is also notable for the post-Revolutionary War confrontation between Sinclair and Brigadier General (later Chief Justice) John Marshall. On July 22, 1794, Marshall led a troop of cavalry up to the front of this house in a failed attempt to arrest Sinclair for supposedly continuing his wartime escapades.

Reynolds Drive
The twisting and narrow Reynolds Drive is listed on 18th century maps as the “Road to Smiths Neck.” It was this route that British troops reportedly marched along to reach Colonel Josiah Parker’s home of Macclesfield under orders to destroy it. The record is unclear, but a report indicates the British troops decided not to burn the Parker home when they found only his family there – not him.

Macclesfield
Named for the Parker Family’s home estate in England, Macclesfield plantation was a 1638 land grant by King Charles I to Josiah Parker’s great-great grandfather. Macclesfield remained the Parker residence during the Revolutionary War when Josiah Parker served under George Washington commanding the Fifth Virginia Regiment in the battles of Trenton, Princeton and Brandywine Creek. The family cemetery still stands near where Macclesfield once was and Josiah Parker himself is reportedly buried there along with the ceremonial sword accepted from Hessian Colonel Johannes Rawl on December 26, 1776, following their surrender after the Battle of Trenton, New Jersey.

Mallory Todd House
Although not a member of the Continental Navy, shipping merchant Mallory Todd of Smithfield was a significant provider of provisions and supplies to the patriot Continental forces. His home still stands in the Town of Smithfield and was once his base of operations as his shipping interests expanded to meet the demands of supply for local patriot forces. He is recognized by the Sons of the American Revolution as a significant contributor to the Revolutionary cause. He is buried in a marked gravesite in the cemetery of the West Parish Church near Wrenn’s Mill in Isle of Wight County.

Local Events

Thanks! It Has Pockets!Thanks! It Has Pockets!
January 12, 2025 - January 12, 2025
Isle of Wight County

The word pocket comes from a French word meaning pouch. A version of pouch-type pockets persisted for millennia until the 16th century when they were ... Read More

LUNCH & LEARN: 1781 Battle of Mackie’s MillLUNCH & LEARN: 1781 Battle of Mackie’s Mill
January 16, 2025 - January 16, 2025
Isle of Wight County

Today is the 244th anniversary of the Revolutionary War engagement between local patriot militia forces and British regular soldiers under Benedict Ar... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
February 02, 2025 - February 02, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

George WashingtonGeorge Washington's Birthday
February 22, 2025 - February 22, 2025
Isle of Wight County

Join us for a presentation about the life and times of the United States’ first president. Afterwards, we will walk to his statue on Main Street and... Read More

Fort Boykin Walking TourFort Boykin Walking Tour
February 22, 2025 - February 22, 2025
Isle of Wight County

Fort Boykin has been a part of American history since 1623 when a fort known as the Castle was constructed following the 1622 Indian Attack. Today, Fo... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
March 02, 2025 - March 02, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

Isle of Wight Courthouse Complex Walking TourIsle of Wight Courthouse Complex Walking Tour
April 05, 2025 - April 05, 2025
Isle of Wight County

Join us as we explore this 18th, 19th, 20th and 21st century site and share the story of its beginnings as well as a few tales of capers and duels. Th... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
April 06, 2025 - April 06, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
May 04, 2025 - May 04, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

LUNCH & LEARN: Happy 274th Birthday, Josiah Parker!LUNCH & LEARN: Happy 274th Birthday, Josiah Parker!
May 09, 2025 - May 09, 2025
Isle of Wight County

Born May 11, 1751, in Isle of Wight County, Josiah Parker was an American politician, Revolutionary War officer, local militia commander, member of th... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
June 01, 2025 - June 01, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

Independence Day Bell RingingIndependence Day Bell Ringing
July 04, 2025 - July 04, 2025
Isle of Wight County

In conjunction with the Virginia American Revolution 250 Commemoration, all Virginians are encouraged to join in a statewide Independence Day bell-rin... Read More

Isle of Wight Courthouse Complex Walking TourIsle of Wight Courthouse Complex Walking Tour
July 19, 2025 - July 19, 2025
Isle of Wight County

Join us as we explore this 18th, 19th, 20th and 21st century site and share the story of its beginnings as well as a few tales of capers and duels. Th... Read More

LUNCH & LEARN: John Sinclair v. General John Marshall, 1794LUNCH & LEARN: John Sinclair v. General John Marshall, 1794
July 22, 2025 - July 22, 2025
Isle of Wight County

Today is the 231st anniversary of the town's second most dramatic event—the confrontation between accused "privateer" John Sinclair and U.S. Cavalry... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
August 03, 2025 - August 03, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

Hessians in Isle of Wight CountyHessians in Isle of Wight County
August 14, 2025 - August 14, 2025
Isle of Wight County

The term "Hessian" refers to the approximately 30,000 German troops hired by the British to help fight during the American Revolution. Today, on the 2... Read More

LUNCH & LEARN: Joyeux Anniversaire, Marquis de Lafayette!LUNCH & LEARN: Joyeux Anniversaire, Marquis de Lafayette!
September 06, 2025 - September 06, 2025
Isle of Wight County

Today in 1757, the Marquis de Lafayette was born. Join us for this event...and a celebratory dessert. On the 267th anniversary of Lafayette’s birth,... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
September 07, 2025 - September 07, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

LUNCH & LEARN: Happy Birthday, U.S. Navy!LUNCH & LEARN: Happy Birthday, U.S. Navy!
October 10, 2025 - October 10, 2025
Isle of Wight County

Today—in advance of the October 13 anniversary—we recognize the beginning of the United States Navy with the story of Isle of Wight County’s own... Read More

Isle of Wight Courthouse Complex Walking TourIsle of Wight Courthouse Complex Walking Tour
October 18, 2025 - October 18, 2025
Isle of Wight County

Join us as we explore this 18th, 19th, 20th and 21st century site and share the story of its beginnings as well as a few tales of capers and duels. Th... Read More

Windsor Castle Walking TourWindsor Castle Walking Tour
November 02, 2025 - November 02, 2025
Isle of Wight County

From the site's pre-colonial existence to the present day, Windsor Castle tells the fascinating history of the development of Smithfield. Join us for ... Read More

Fort Boykin Walking TourFort Boykin Walking Tour
December 06, 2025 - December 06, 2025
Isle of Wight County

Fort Boykin has been a part of American history since 1623 when a fort known as the Castle was constructed following the 1622 Indian Attack. Today, Fo... Read More

LUNCH & LEARN: Battle of Great BridgeLUNCH & LEARN: Battle of Great Bridge
December 09, 2025 - December 09, 2025
Isle of Wight County

The Battle of Great Bridge took place on December 9, 1775, in Great Bridge over a narrow bridge that crossed the southern branch of the Elizabeth Rive... Read More

Contact

Judy Winslow