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  • Writer's pictureTim Murphy

The Virginia Capital Trail

The Virginia Capital Trail (VCT) is a 51.7-mile bike route that extends from Jamestown to Richmond, Virginia. Though recently completed in 2015, the VCT passes by several dozen historic landmarks and attractions, encompassing centuries of American history. According to the Richmond Times-Dispatch, over 1.2 million people visited the VCT last year, making it one of the most popular trails in Virginia.

Mile 0 – Jamestown: I began my journey just after 7:00 a.m. at the VCT’s eastern terminus near Jamestown Settlement—a living history museum that depicts the defining social, cultural, and economic characteristics of England’s first permanent colony in America. Jamestown was established in 1607 as the capital of Virginia, a prosperous distinction it held for over ninety years. However, when government officials moved the seat of power to Williamsburg in 1699, Jamestown experienced a period of rapid socioeconomic decline. By the mid-18th century, the town was virtually abandoned. Today, only the ruins of the original settlement exist, but they are open for exploration at Historic Jamestowne, located one mile south of Jamestown Settlement.

Mile 0.7 – Green Spring: After departing from Jamestown, I biked through the fields that once witnessed the Battle of Green Spring—the last major land battle of the Revolutionary War prior to the Siege of Yorktown. In June 1781, five thousand British troops under General Charles Cornwallis marched into Williamsburg after a demoralizing campaign in the Carolinas. The British commander sought to establish a base of operations in the neighboring city of Portsmouth, where he could resupply his troops and receive reinforcements from General Henry Clinton in New York. Unfortunately for Cornwallis, the only way to access Portsmouth was by crossing the James River—a maneuver that would leave his army vulnerable to attack by Marquis de Lafayette and his pursuing Patriot forces.

However, Cornwallis was deliberate in his approach. He would merely stage a river crossing—sending only his baggage train and the Queen’s Rangers across—while the rest of his army garrisoned the wooded ravines along Green Springs Road. There, Cornwallis hoped to annihilate the opportunistic Continentals and effectively end any major resistance to Britain’s Southern Strategy.

On the morning of July 6, 1781, Cornwallis dispatched several “deserters” to the American lines with faulty information of a full-scale river crossing. Upon hearing this news, Major General Anthony Wayne, commander of the Continental Advance Guard, rode out towards Green Spring to observe the British activity. Lafayette joined Wayne later that afternoon, and after some discussion, the two commanders agreed to attack the seemingly disadvantaged enemy force.

At 3 p.m., Wayne led nearly nine hundred soldiers (most of whom Virginia and Pennsylvania militiamen) towards the James River along Green Springs Road. They engaged with British pickets for nearly two hours before capturing an abandoned enemy cannon. However, this gun—strategically positioned in an open field—was intentionally left behind under Cornwallis’s orders; its seizure signaling the British counterattack. Around 5 p.m., British artillery unleashed a barrage of canister and grapeshot upon the unprotected Continentals, inflicting heavy casualties. British infantry, commanded by Lieutenant Colonels Banastre Tarleton and Thomas Dundas, then charged the disjointed American formations.

Amidst the mayhem, Wayne managed to reorganize his lines and ordered his men to charge the approaching Redcoats with fixed bayonets. The Americans were overwhelmingly outnumbered nearly five-to-one, but their audacious response momentarily halted the British advance. After several volleys of close-range musket fire, the battered Continental army swiftly made its retreat. Cornwallis, pleased with his army’s performance, decided not to pursue. The British recorded 75 casualties while the Americans suffered 150.

Wayne’s composure and dauntless maneuvering undoubtedly saved the Continental army from utter disaster; however, the sheer recklessness and perceived impudence of his actions garnered some contentious criticism. One of Wayne’s detractors, Doctor Robert Wharry, published the following synopsis in the New Jersey Gazette, which only further immortalized the general’s frenzied reputation: “another Blockhouse affair—Madness — Mad Anthony, by God, I never such a piece of work heard of — about eight hundred troops opposed to five or six thousand veterans on their own ground.”

At Mile 2, the trail adjoins State Route 5—a Virginia Scenic Byway that connects Williamsburg to Richmond—which runs alongside the VCT for the next 46 miles. At times, the divide between the road and trail measures less than ten feet, so be cautious when navigating these stretches of close proximity. At Mile 7, I biked by Chickahominy Riverfront Park and over the bridge spanning the river. Standing nearly fifty feet above the water, this overpass is an excellent place to observe some stunning views of the mighty Chickahominy. The next eight miles along the trail are fairly straight and unremarkable.

Mile 15.5 – Fort Pocahontas: Just south of Mile Marker 15 stands Fort Pocahontas. Engineered by Brigadier General Godfrey Weitzel in May 1864, the fortifications were designed to protect Union vessels along the James River during the Bermuda Hundred Campaign. Garrisoned within its walls were 1,100 men from Brigadier General Edward A. Wild’s brigade—consisting of the 1st, 10th, 22nd, and 37th regiments of United States Colored Troops (USCT) and the 2nd Colored Light Artillery—and Brigadier General Edward W. Hinks’s 3rd Division of the XVIII Corps, also comprised entirely of USCT.

On May 24, 2,500 Confederate cavalrymen under Major General Fitzhugh Lee attacked the ramparts of Fort Pocahontas, which were still under construction at the time. The Union pickets fled as the mounted enemy charged towards the incomplete Federal fortifications. At 12:30 p.m., when the Confederates reached the wood line bordering Fort Pocahontas, Lee ordered his men to dismount and charge the fort. As the Confederates advanced, General Wild instructed his troops not to fire until the enemy reached the abatis surrounding their position. The defensive works stymied the Confederate charge and the Union army responded with a torrent of lead, tearing through the stagnant rebel lines. A ninety-minute firefight ensued before the Confederate forces retreated into the woods.

Lee organized his second attack at 2:30 p.m. While leading a provisionary assault against Fort Pocahontas’s strongest point, Lee anticipated that Wild would divert troops from the fort’s weaker, unfinished section, thereby creating an opportunity to flank and infiltrate the Union stronghold. However, the Federals firmly held their position as the Confederates mounted their second charge. The gray surge came within thirty feet of Fort Pocahontas’s walls before Lee ordered a retreat shortly after dusk. Union forces inflicted 140 casualties while suffering just 22 of their own. This battle, known as the Action at Wilson’s Wharf, is historically significant, as it is the only Civil War battle in which the majority of Union forces were colored troops.

During the Siege of Petersburg, Fort Pocahontas was utilized as a prison for Confederate sympathizers and a refuge for escaped slaves. Following the war, the fort became the headquarters for the Freedmen’s Bureau of New Kent and Charles City, which helped emancipated individuals register to vote, obtain marriage licenses, reunite families, and establish schools. Today, Fort Pocahontas can only be toured by appointment or during their annual reenactments each June.

Mile 16.5 – Sherwood Forest: After an hour-and-a-half of continuous pedaling, I finally reached my first historic attraction: John Tyler’s Sherwood Forest. Prior to his acquisition of the estate, Tyler was William Henry Harrison’s running mate on the Whig ticket for the 1840 General Election. The duo, known as “Tippecanoe and Tyler Too,” handedly defeated Democrat Martin Van Buren and were sworn into office on March 4, 1841. Unfortunately, Harrison’s term as President abruptly ended when he succumbed to pneumonia just one month later.

Harrison’s sudden death placed the U.S. government in unchartered territory. Never before had a President died in office, and although there were rules of succession already in place, they had never been implemented nor collectively interpreted. While some legislators argued the Vice President should act as a “caretaker” to the presidency, Tyler believed he should claim full powers of the position. On April 6, 1841, Tyler took the oath of office at the Brown’s Queen Indian Hotel in Washington, D.C., thereby assuming the presidency and setting the standard of succession for years to come.

Tyler’s interpretation of constitutional law and hasty ascension to power rubbed many politicians the wrong way, especially those in his own party. He was ostracized by the Whigs and ridiculed as “His Accidency” throughout his term. Though intended as insults, Tyler embraced his portrayal as a political outlaw, likening himself to Robin Hood. This comparison is characterized in his estate’s name ‘Sherwood Forest’—a tribute to Robin Hood’s fabled English sanctuary.

Tyler lived at Sherwood Forest with his second wife, Julia Gardiner Tyler, and their children from 1845 until his death on January 18, 1862. During the Civil War, Union soldiers twice occupied Sherwood Forest’s property, once during McClellan’s Peninsula Campaign of 1862 and again during Grant’s Overland Campaign of 1864. Today, the estate encompasses fifty acres and remains under the ownership of Tyler’s descendants—the only presidential home in the nation that has been continuously occupied and maintained by a president’s family.

A $10 donation is required for a self-guided grounds tour, which leads you around the manor home (measuring an impressive 304-feet long) and other original structures dating from the 1680s to 1850s. Behind the main house sits 25 acres of terraced gardens and manicured land designed by renowned 19th-century horticulturist Andrew Jackson Downing. Situated in the front yard is John Tyler’s proposed gravesite. When Tyler died in 1862, Union forces occupied his property. Due to his involvement in the Confederate Congress, Tyler’s remains were unable to be interred at Sherwood Forest or brought to Washington D.C. Instead, he was buried at Hollywood Cemetery in Richmond, Virginia, underneath a Confederate flag. John Tyler’s unorthodox political career and provocative personal life certainly warrant more investigation, so stay tuned for a future article reviewing our 10th President.

Mile 18.7 – North Bend and Kittiewan Plantations: About two miles from Sherwood, I veered off the trail down Weyanoke Road to visit two historic Antebellum plantation houses, the first being North Bend. Built in 1801, North Bend Plantation was originally home to John Minge and his wife, Sarah Harrison, the sister of President William Henry Harrison. In 1843, the estate was sold to Thomas H. Wilcox, who subsequently fled North Bend at the onset of the Civil War.

In June 1864, General Philip Sheridan established his headquarters here while 30,000 Federal troops prepared to cross the James River at Weyanoke Point a half-mile upstream. On the evening of June 14, army engineers feverishly constructed enough pontoons to span seven hundred yards across the might James in just under eight hours. This spectacular feat of engineering helped the Union army transition from the Overland Campaign to the Siege of Petersburg.

Following the war, North Bend passed through several owners before George Forbes Copland acquired the property in 1916. Today, his descendants still tend the 850-acre farm and operated a bed and breakfast inside the plantation house.

Adjacent to North Bend is Kittiewan Plantation, which once belonged to the family of Dr. William Rickman, the Director of Continental Hospitals of Virginia from 1776 to 1780. By the time of the Civil War, Dr. William Selden owned the property. Much like North Bend, Kittiewan was commandeered by Federal troops as they prepared to cross the James River in June 1864. Today, the estate belongs to the Archaeological Society of Virginia; however, the mid-18th century manor house is currently under renovations and closed for tours.

Mile 20 – Charles City Court House: At 11 a.m., I reached Charles City Court House, the third-oldest surviving courthouse in the country—continuously used for judicial purposes since 1757. Contrasting from law and order, the building has been the setting for some violent encounters throughout American history. In January 1781, Lieutenant Colonel John Simcoe and the Queen’s Rangers ambushed an American militia stationed at the courthouse. The Americans lost twenty men killed, captured, or wounded in the surprise attack, while Simcoe’s Rangers suffered only three wounded.

During the Civil War, the courthouse fell between Union and Confederate control several times. In December 1863, Union cavalrymen captured the courthouse and ninety soldiers belonging to the 24th Virginia Cavalry, one of whom was discovered to be a woman disguised as a man.

Perhaps the most brutal encounter at Charles City Court House occurred on April 6, 1892, when 75 masked men apprehended and lynched Isaac Brandon—an African American man charged with assaulting a white woman—from a large tree in front of the judicial building. According to the Roanoke Times, Brandon allegedly “broke into a house…occupied by three ladies, and, with threats to kill them, assaulted one of them.” He was awaiting trial in the adjacent jailhouse when the vigilante mob exacted their premature revenge in a manner not-so-uncommon for the Jim Crow South. Brandon left behind a wife and eight children and none of his assailants were ever brought to justice.

Mile 25.3 – Westover Church: Following a brief snack break in Charles City, I arrived at Westover Church around noon. Founded in 1731, this was the second church of the Westover Parish, which was established over a century earlier in 1625. Following the disestablishment of the Anglican Church in 1784, Westover Church experienced a sharp congregational decline. The residual resentment towards Anglicans and ex-Loyalists in the wake of the Revolution forced many clergymen and parishioners to flee. By 1803, the church stood abandoned.

In 1833, religious services were reintroduced to Westover Church; its structure renovated after three decades of deterioration. However, the house of worship was damaged once again during the Peninsula Campaign of 1862. Union troops who occupied the church grounds vandalized the landscape, used headstones as tent floors, and converted the oratory into a stable. Despite its mistreatment, Westover Church survived the war and was completely restored by 1867. Episcopal services continue to this day.

Mile 27 – Berkeley Plantation: After passing Mile Marker 27, I turned left onto Herring Creek Road and biked until I reached the gravel entrance to Berkeley, “Virginia’s most historic plantation.” Berkeley was patented on December 4, 1619, by Captain John Woodlief and 37 members of the Berkeley Company. Upon landing ashore, Woodlief led his men in a prayer of thanksgiving and arranged a feast commemorating their safe passage. This celebration—as ordained by King James I in the Company’s charter—was to be repeated annually thereafter, making it the first observance of Thanksgiving in America, nearly two years before the Pilgrims.

Unfortunately, this jovial tradition did not last long. On March 22, 1622, Chief Opechancanough of the Powhatan Confederacy launched a series of surprise attacks against the English settlers. Three hundred forty-seven colonists were massacred across the Virginia colony, eleven of which were slain on Berkeley’s soil. The threat of future insurgency forced the remaining settlers to abandon the Berkeley Hundred and retreat towards Jamestown. Berkeley remained vacant until 1636 when it was re-patented by Theodorick Bland.

In 1691, Berkeley was purchased by Benjamin Harrison III, who vastly expanded business operations around the plantation. He constructed the first commercial shipyard on the James River and utilized its fleet to transport Berkeley tobacco to England. When Benjamin IV inherited Berkeley in 1710, the Harrison family was one of the wealthiest in Virginia.

It was Benjamin IV who oversaw the construction of Berkeley’s manor house. Built between 1721 and 1726, the impressive Georgian-style mansion was assembled with materials sourced from the plantation grounds (excluding the original brass detailing) and is believed to be the oldest three-story brick home in Virginia.

When Benjamin IV died suddenly in 1745, Berkeley Plantation was passed to his son, Benjamin V. The inherent Harrison was a budding political protégé at the time of his primogeniture. He was elected to the Virginia House of Burgesses in 1749, but had to wait an additional three years to claim his burgess seat as he was underage. Benjamin V served in the Virginia General Assembly from 1752 until 1774, when he attended the First Continental Congress as a representative of Virginia.

Harrison was well-respected among his fellow congressmen. During the Second Continental Congress, he was frequently appointed Chairman of the Committee, presiding over the final debates concerning the Lee Resolution—distinguishing the thirteen colonies as “free and independent states.” On July 1, 1776, Harrison was selected to read aloud Thomas Jefferson’s draft of the Declaration of Independence to the delegation. On August 2, Benjamin Harrison V was one of 56 representatives to sign the landmark resolution.

Harrison’s efforts for independence were seen as traitorous by British supporters. Like many Declaration signers, Harrison was a conspicuous target for Loyalist forces. In January 1781, 1,600 British troops commanded by turncoat Benedict Arnold sailed up the James River, threatening to invade Berkeley. Harrison managed to flee with his family to Richmond before the Redcoats arrived, leaving his estate at the mercy of enemy forces, who subsequently ransacked the house—burning all of Harrison’s furniture and family portraits—and destroyed all crops and livestock. When the Harrison family returned in 1784, Berkeley was in utter ruin. It took Benjamin V four years to restore his livelihood.

When Benjamin V died in April 1791, Berkeley was bequeathed to his oldest son, Benjamin VI. His youngest son, William Henry Harrison—the future 9th President of the United States—was just beginning his medical studies at the University of Pennsylvania. The passing of the Harrison family patriarch left young William with insufficient funds to continue schooling, so he abandoned medical practice for what would become a distinguished military career.

Benjamin VI died in 1799, leaving Berkeley to Benjamin VII, who was only twelve years old at the time. The residual effects of the Revolution, in conjunction with poor farming practices, caused the plantation to spiral into financial ruin. Dr. Benjamin Harrison VIII was the last Harrison to own Berkeley before it was sold out of the family in the 1860s.

During the Peninsula Campaign of 1862, over 100,000 soldiers from the Union Army of the Potomac organized their camps around Berkeley Plantation. General George B. McClellan established his headquarters on the upper floor of the manor house while the ground floor was used as a hospital and the basement a prison for Confederate POWs.

While encamped at Berkeley, General Daniel Butterfield composed the army’s first official bugle call, “Taps.” Originally intended to signal lights out, “Taps” was first commissioned by Captain John C. Tidball to play during a burial for one of his cannoneers. Since 1891, the solemn song has been a standard component of military funerals and evening flag ceremonies at military bases.

Following the Civil War, Berkeley fell into a state of disrepair. In 1907, John Jamieson, a former drummer boy in McClellan’s army, purchased the estate and its surrounding 1,400 acres for $28,000. His son, Malcolm, inherited the property in 1927. He, along with his wife, Grace, spent the next several years extensively restoring Berkeley to its 18th century appearance. In 1938, the estate was opened to the public for tours.

Today, Berkeley Plantation—the ancestral home of Presidents William Henry Harrison (9th) and Bejamin Harrison (23rd)—is one of the most beautiful estates on the James River. General admission for the Berkeley estate costs $15, which includes a guided tour of the mansion’s first floor and access to the plantation’s gardens, monuments, and outbuildings. Much like Sherwood Forest, Berkeley’s history cannot be thoroughly reviewed in this brief synopsis. Therefore, an additional article is necessary to fully appreciate the estate’s significance in American history.

Mile 27 – Westover Plantation: After departing from Berkeley, I made a sharp right onto Westover Road and continued for three miles until I arrived at Westover Plantation. Established in 1619, Westover was most likely named after Henry West, son of Sir Thomas West, 3rd Baron De La Warr and former Governor of the Virgina colony. The plantation’s first recorded owner was Captain Thomas Pawlett, who patented the property in 1637. In 1688, Westover was acquired by William Byrd I. Sixteen years later, Westover was passed to his son, William II, who would later gain prominence as the founder of Richmond, Virginia.

Westover’s magnificent manor home was constructed by William Byrd III circa 1750. Despite his family’s affluence, William III developed a nefarious gambling addiction, which brought his family on the brink of bankruptcy. Severely troubled by his debts, Byrd committed suicide on New Years’ Day, 1777. William’s landholdings were passed to his widow, Mary, who sold much of them off to repay her late husband’s liabilities and keep Westover in good standing. Upon her death in 1814, Westover was sold out of the Byrd family.

In July 1862, following the Seven Days’ Battles, Westover became the headquarters for General Fitz John Porter and the Union 5th Corps. On August 1, the plantation came under heavy fire from Confederate artillery across the river at Coggins Point. The bombardment resulted in 25 Union casualties and the destruction of Westover’s 4,000-volume library.

In 1866, Westover was sold to Augustus H. Drewry, a Confederate officer who commanded the batteries at Fort Darling during the Battle of Drewry’s Bluff in May 1862. After Drewry’s death in 1899, the plantation was purchased by Claire Sears Ramsey, a descendant of the Byrd family who instrumentally refurbished and modernized the house. In the early 20th century, Westover was purchased by Richard Teller Crane II—the first U.S. diplomat to Czechoslovakia—whose family has maintained the estate ever since.

Westover displays some of the nation’s finest examples of Georgian architecture while simultaneously offering unparalleled views of the James River. The estate also features several outbuildings and a formal garden, which contains the tomb of William Byrd II. A self-guided grounds tour costs $5 per person; however, visitors wishing to explore the mansion itself must make reservations ahead of time and pay a $25 admittance fee.

Mile 30 – Shirley Plantation: At 3 p.m., I arrived at Shirley—Virginia’s first plantation. Shirley and its surrounding lands were patented in 1613 by Sir Thomas West, 3rd Baron De La Warr, who planted tobacco for the Virginia Company of London. Following West’s death in 1618, portions of his original 4,000-acre claim were sold off to prospective cultivators. In 1638, Colonel Edward Hill I purchased a 450-acre parcel, establishing Shirley’s first generation of Hill-Carter occupation.

By 1720, Edward Hill III was in possession of Shirley. His only male heir, Edward IV, died of consumption several years prior, which meant the plantation would be passed down to his youngest daughter, Elizabeth. In 1723, she married John Carter—the son of Robert “King” Carter—who assumed possession of Shirley following Edward III’s death three years later. That same year, ground was broken for Shirley’s Great House. The iconic mansion was completed in 1738.

By 1800, the Carter family owned 195 slaves at Shirley and an additional 590 across dozens of other plantations, making them Virginia’s largest slaveholders. When the Civil War broke out in April 1861, Shirley’s owner, Hill Carter, and his six sons joined the Confederate army. In their absences, the plantation was managed by Hill’s wife, Mary, and their daughters. In July 1862, several hundred wounded Union soldiers established a field hospital on Shirley’s property following the Battle of Malvern Hill. The women of Shirley actively assisted the Federal casualties, a kindness that prompted General McClellan to issue a Federal Order of Safeguard, which spared Shirley from destruction for the duration of the war.

Today, Charles Hill Carter III and his family—the 11th and 12th generations of Hill-Carters—continue to cultivate Shirley’s farmland and occupy the second and third levels of the Great House. Visitors wishing to see Shirley’s splendor can tour the mansion’s first floor and its surrounding estate for an admission fee of $25 (or $11 for grounds only).

Mile 34 – Malvern Hill: At the end of June 1862, the Union Army was on the brink of collapse. Though on the doorstep of Richmond, McClellan’s troops were unable to circumvent the Confederate defenses, suffering heavy casualties at the battles of Gaines’ Mill and Savage’s Station days prior. Battle-weary and encumbered, Federal forces under General Fitz John Porter established a defensive position upon Malvern Hill, anxiously awaiting the final Confederate assault.

On the morning of July 1, 70,000 Confederate soldiers approached Malvern Hill, ready to engage nearly 80,000 Union troops spread across a 1.5-mile front. At 10 a.m., Confederate artillery opened fire on the Union positions in an ineffective, piecemeal barrage. The rebel batteries—which operated independently of one another—were unable to concentrate fire, giving the Union guns opportunity to find their ranges and suppress active elements of the Confederate army.

After several hours of bombardment, there was brief lull from the Union cannons. Believing his artillery had overwhelmed the Federals, General Robert E. Lee called for an infantry assault. Sixty-five hundred men under Generals D.H. Hill and Stonewall Jackson motioned towards the Union center, while General John B. Magruder mobilized 5,000 men to flank the Union left. However, Magruder made a logistical error and took the wrong road, which delayed his arrival by a costly couple of hours. When Magruder’s forces reached the battlefield at 5:30 p.m., the Confederate assault led by Jackson and Hill had already failed. But this information had not been communicated with Magruder, who ordered his men to charge the Union left flank, unwittingly advancing them into open fields within sight of the U.S. artillery. The Federal guns unleashed a devastating cannonade that decimated the Confederate ranks as they neared Union lines.

The final Confederate assault took place at dusk and involved the brigades of Paul Jones Semmes and Joseph Kershaw, who once again attempted to break the Union left. As darkness and smoke blanketed the battlefield, confusion ensued—fueled by muddled sounds and indistinguishable shadows. Kershaw’s men, who had mistakenly advanced past the Confederate line, were subjected to a crossfire between hostile and friendly forces, inflicting significant casualties. Considering the formidable Federal position and the recent chaos across the battlefield, Lee chose to abandon his assault. The Battle of Malvern Hill resulted in nearly 8,500 casualties—3,000 Federals and 5,500 Confederates—and a decisive tactical victory for the Union army. However, despite the outcome, McClellan decided to withdraw his troops to Harrison’s Landing (Berkeley Plantation), conceding a strategic victory to Lee and effectively ending the Peninsula Campaign.

Mile 38 – Gravelly Hill: Just outside of Varina, I biked through an area called Gravelly Hill—a free slave settlement established by Robert Pleasants in 1799. Despite being the descendant of a wealthy, plantation-owning family, Robert was a longtime antislavery advocate who embraced the teachings of Anthony Benezet and other like-minded individuals of the Quaker faith. Robert’s father, John Pleasants III, was also influenced by this ideology. Following his death in 1771, John stipulated in his will that his family’s slaves be freed when they reached thirty years old; however, this request was contingent upon forthcoming legislative changes as manumission was still illegal in Virginia at the time.

As executor of his father’s will, Robert tirelessly petitioned the Virginia General Assembly to amend their archaic laws. His efforts paid off when the Assembly passed the Manumission Act of 1782, which allowed slaveowners to free their slaves without government approval. The ratification of this law allowed legal manumission of Pleasants’ slaves; however, other members of the Pleasants family refused to honor the late John’s wishes, keeping their slaves in bondage.

In 1797—after fifteen years of failed attempts to free his father’s slaves—Robert filed lawsuits against family members who opposed manumission. John Marshall represented Robert Pleasants on behalf of the slaves while Chancellor George Wythe oversaw the landmark proceedings known as Pleasants v. Pleasants. After tense deliberations, Wythe ruled in favor of Robert Pleasants on September 12, 1798. He ordered the defendants to immediately emancipate all slaves who qualified under the will’s provisions and pay reparations to those wrongfully detained. The defendants appealed to the Virginia Court of Appeals in 1799.

Upon review, the appellate court upheld the lower court’s decision regarding manumission but rejected its notion for restitution payments. Nevertheless, freedom prevailed. One hundred eighty-six of Pleasants’ slaves qualified for immediate emancipation, while nearly 250 others achieved their legal right to freedom in later years. Pleasants v. Pleasants is recognized today as the largest manumission trial in United States history.

Following the landmark decision, Robert Pleasants took additional steps to support his family’s former slaves. Upon his death in 1801, Robert willed his 350-acre Gravelly Hill estate and a substantial endowment of money to establish a school “for the benefit of the Children and descendants of who have been Emancipated by me, or other black Children whom they may think proper to admit.” This led to the creation of the Gravelly Hill School—the first school for free blacks in Virginia.

Mile 39 – The Battle of New Market Heights: Past the signs for Fort Harrison are several placards commemorating the Battle of New Market Heights. On the evening of September 28, 1864, Major General Benjamin Butler’s Army of the James crossed the James River to assault Confederate defenses along New Market Road. The Union XVIII Corps under Major General Edward Ord was deployed to Fort Harrison while Major General David B. Birney’s X Corps moved north towards Deep Bottom Bridge.

Spearheading the X Corps’ advance were three USCT brigades under Brigadier General Charles Paine. In command of each brigade were Colonels Samuel Duncan, Alonzo Draper, and John Holman. At 4 o’clock the following morning, Paine’s men organized battle formations behind Four Mile Creek and commenced their assault against the imposing Confederate defenses atop New Market Heights. As the three brigades advanced, they encountered some challenging geography—having to cross a quarter mile of swampy terrain, navigate a heavily-wooded ravine, and brave nearly three hundred yards of open, obstacle-laden field to reach the Confederate defenses. Due to these impediments, the once-coordinated Union advance became rather disjointed.

Colonel Duncan’s brigade, consisting of the 4th and 6th USCT, was the first to reach New Market Height at 5:30 a.m. As the 4th USCT attempted to cross the outer line of abatis surrounding the rebel earthworks, members of Lieutenant Colonel Frederick Bass’ Texas-Arkansas Brigade unloaded their rifles unto the vulnerable Union attackers. Entangled with no additional military support, the USCT were decimated by unrelenting fire. Fifty percent of Duncan’s brigade were listed as casualties following the initial assault, with Duncan himself being wounded four times.

Colonel Draper’s brigade arrived shortly after Duncan’s repulse. By now, the 3rd Richmond Howitzers and Rockbridge Artillery were showering the Union army with ordinance, making any attempt of advance suicide. After about an hour, the Confederate bombardment began to subside. Seizing the opportunity, Draper ordered his men to charge the earthworks. Members of the 5th, 36th, and 38th USCT were the first to breach the Confederate fieldworks, only to find that most of the enemy had withdrawn to their secondary defenses along Varina Road.

The Battle of New Market Heights was a costly victory for the Union. General Paine lost nearly one-third of his men during the assault while the 1,800 Confederate defenders suffered only fifty casualties. However, the bravery and heroism displayed by USCT on both fronts of Butler's offensive were crucial to the operation’s ultimate objective—forcing Lee to divert troops from Petersburg to Richmond, weakening the Cockade City’s defenses. In recognition for their courage on this battlefield, fourteen black soldiers were awarded the Medal of Honor.

I entered Four Mile Creek Park at mile 39.5 and biked along its periphery for an additional mile before taking the underpass below I-295. Between miles 42 – 49, the trail’s scenery transitions from wooded countryside to bustling suburbia, embroiled with construction zones and heavy automobile traffic. However, a good portion of this unsightly stretch is downhill, so it goes by rather quickly.

Mile 50 – Rocketts Landing: Named for Robert Rockett—a ferry operator from the 1730s—Rocketts Landing was originally established as a commercial/residential district for merchants and tenant laborers. Home to immigrants, Jews, and freed blacks, this culturally diverse area evolved into one of America’s busiest inland ports between 1790 and 1830. During the Civil War, Rocketts Landing was occupied by the Confederate Navy. Its shipyard was used to build and service vessels for the James River Squadron, particularly its ironclad gunboats.

In 1866, David G. Yuengling founded the James River Brewery at Rocketts Landing. Although the brewery closed only thirteen years later, its brick “beer caves” can still be seen from behind chain link fences along the trail. While Yuengling’s enterprise was left abandoned, other structures at Rocketts Landing have been given new life. For instance, the building which once housed the Richmond Cedar Works Manufacturing Company—which produced ice chests and ice cream makers between 1884 and 1967--has been renovated into condos. Additionally, the old Power Plant building, which operated the Richmond Union Passenger Railway—America’s first all-electric trolley system—now functions as the Boathouse Restaurant.

Mile 50.6 – Great Ship Lock Park: Located on Chapel Island, the Great Ship Lock was originally one in a series of wooden locks engineered by the Richmond Dock Company in 1816. The shallow waters of the James River necessitated construction of the canal system to improve upriver navigation and promote commerce at the city’s shipping terminals. In 1854, the James River Company purchased and improved the canal system—replacing the wood locks with granite and connecting the Great Ship Lock to the James River Kanawha Canal—creating the “Tidewater Connection.”

The decline of the Richmond’s canal era arrived in 1877 when the Chesapeake and Ohio Railroad constructed its first lines along Dock Street. The canals rapidly lost business to the locomotive’s superior efficiency and transportation capacity, becoming defunct by the 1880s. While the canals lost business, the area remained quite industrious. From 1898 to 1906, Chapel Island was the location of the Trigg Shipyard, which produced war vessels for the U.S. Navy. Its most famous ships were the USS Dale (DD-4) and USS Decatur (DD-5)—Bainbridge-class destroyers that served in the American Patrol Squadrons during World War I. Though no longer used for maritime affairs, the Great Ship Lock is still operational and free to be explored along with eleven acres of Chapel Island.

Across from the Great Ship Lock is Tobacco Row—a cluster of repurposed warehouses reminiscent of Richmond’s tobacco manufacturing past. Most of these buildings date between 1886 and 1929, as many older structures were destroyed during the Evacuation of Richmond in April 1865.

Once located on Tobacco Row was Libby Prison. Prior to its notoriety as a jail, the three-story brick warehouse was known as the Libby Ship Chandlery—a grocery store owned by Captain Luther Libby and his son, George. In 1861, the Confederate military commandeered the building and converted it into a prison for Union officers. Overcrowding, starvation, and disease soon became rampant, causing many inmates to perish. Libby earned a horrible reputation due to its high mortality rate, akin to other infamous prison camps like Andersonville and Belle Isle.

The prison survived the burning of Richmond’s warehouse district in 1865, but remained vacant for nearly two decades thereafter, falling further into disrepair. In 1889, the former Libby Prison was purchased by Charles F. Gunther who had the building disassembled and rebuilt in Chicago as a war museum. After failing as a tourist attraction, the prison was dismantled for good; its pieces sold as souvenirs.

I left the Great Ship Lock Park a little after 6 p.m. and biked underneath Richmond’s elevated train trestles until I reached the VCT’s Western Terminus at mile 51.7, just outside of the city’s flood wall. After nearly twelve hours, my trip was finally complete. My overall impression of the VCT is that, while the trail’s corridor is a trove of historic intrigue, the trail itself is just decent. As previously mentioned, the trail parallels a state highway for most of the journey, sometimes coming within six feet of the road. Though Virginia drivers don’t have the best reputation, I trust they won’t go careening onto the bike path; however, the trail’s close proximity to motorists still manages to raise my anxiety ever so slightly.

Another VCT criticism is that many of the “nearby” historical attractions are located several miles off the trail. So, if you’re like me and want to visit every location, plan on adding at least twenty miles to your trip. Also, certain prolonged stretches of the trail (near Westover Church for example) are not very scenic and devoid of trees, making bike travel during the summer months absolutely brutal. Make sure you bring plenty of water and snacks if you choose to explore the VCT on hot days. That being said, there is plenty to discover along the Virginia Capital Trail. And while you could simply drive along VA-5 and visit these places in much quicker time, it’s not the destination but the journey that truly matters. Trail Rating: 6/10.

Visit the Virginia Capital Trail Foundation for more information on the VCT, its amenities, and nearby attractions

Check out the following links for their corresponding historic sites:


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