Nestled in the heart of North Carolina’s Piedmont, Hillsborough is a town where each step along the downtown streets whispers stories from its fascinating past. Its history spans centuries, from Native American roots and the Colonial era, through its pivotal role in the American Revolution and founding of the nation, to the horrors of the Civil War. Today, Hillsborough retains its small-town charm while continuing to be a cultural center. You’ll discover art galleries, historic sites, delicious eateries, scenic hiking trails, and river access. Though it’s only about forty minutes along I-40 from Raleigh to the east and Greensboro to the west, Hillsborough feels like a world away—a perfect adventure, especially for history lovers.
In this series of posts we’re going to travel through time, digging deep into Hillsborough dynamic history, learning about key events in its past and taking time to immerse ourselves in what makes Hillsborough so special today.
Whether you are sipping on a homemade pastry and Joe Van Gogh latte of the day at Cup of Joe while cozying up with a good local read from Purple Crow books, grabbing a granola bar before walking the Eno Riverwalk Trail, or simply meandering through the downtown shops and admiring the 18th-19th century architecture, the history and character of Hillsborough cannot be ignored. It is fitting that Hillsborough sits on what used to be a Trading Path for Native American tribes from the Waxhaw Region near Charlotte all the way up to Virginia and beyond, because Hillsborough’s rich culture comes from a confluence of diverse stories—from Native Americans, to early European settlers, to African Americans—each threading their life stories into the tapestry of the town and its history. It is this diverse mix of heritage that continues to breathe life into this vibrant community.
For thousands of years, this area along the Eno River was inhabited by numerous tribes, including the Siouan-speaking Occoneechi. Famed early explorer John Lawson documented his visit to the area (1701), noting that the Occoneechi were living in a village near the Eno called Oconahowan. They differed from other regional tribes in that they did not have a central government, but rather lived in small clans. Lawson noted about fifty to seventy-five people in Oconahowan when he passed through. They lived in wigwam houses and subsisted on the ‘three sisters’: corn, squash, and beans. Archaeologists have also discovered a significant Yesah Native American Village at the Wall Site near a bend along the Eno River, just east of Hillsborough, dating to roughly A.D. 1400–1600. Visitors to Hillsborough can learn about the Occaneechi-Saponi culture at a reconstructed village site not far from the Eno Riverwalk near downtown.
Hillsborough was a key trading stop along the ancient road known as The Great Trading Path (also the Occaneechi Path). Here, local Siouan tribes like the Saponi and Occoneechee often acted as middlemen in commerce, trading first with the Cherokee and Catawba (who were traditional enemies) and then with the arriving Europeans. We’ll be digging deeper into the fascinating history of the Occaneechi in a future ‘History Trails’ feature!
The North Carolina Piedmont, though rich in resources, was not inhabited by European settlers until the 1740s. Hillsborough is in an area once referred to as the ‘backcountry’ because rivers like the Eno were not directly navigable to the ocean ports, requiring settlers to portage (carry goods over land). The majority of early settlers came down the ‘Great Road’ from Pennsylvania. Many were Scots-Irish, Moravians, Quakers, and Baptists who sought to escape the vestry acts requiring them to support the Church of England. By the mid-1750s, the cheap land and opportunity led Orange County’s population to grow to around 4,000, quickly establishing Hillsborough and Salisbury as the leading cities in the backcountry.
In 1754, a surveyor for Lord Granville, named William Churton, plotted out the town we now know as Hillsborough. Hillsborough’s Main Street still bears his name as ‘Churton Street.’ It was originally named Corbin Town, then renamed Childsburgh in 1759, and finally became Hillsborough in 1766 after the then-British Secretary of State for the Colonies, the Earl of Hillsborough. While the town gets its name from an Earl, the region’s hilly terrain makes Hillsborough a perfect, fitting name. With this history firmly in place, our first stop in town is the Orange County Old Courthouse and the Old Clock that has kept watch over Hillsborough for over 250 years.
We’re going to start our ‘time-traveling adventure’ at the Old Orange County Courthouse. Since the town’s founding in 1754, Hillsborough has been the primary seat of government for Orange County. While the first courthouse was built in this vicinity in 1756, the current ‘old’ courthouse was completed in 1844.
For any good time-traveling adventure, you need a clock to guide you through the centuries. As we stand at the courthouse square, look up at the historic clock—a working symbol of Hillsborough that connects the past, present, and future. This clock has witnessed over 250 years of history, having been originally given as a gift by King George III to St. Matthew’s Episcopal (then Anglican) Church in 1766.
This clock was ticking through time as the Regulator Movement caused a frenzy of rebellion in the region. The Regulators were backcountry farmers in North Carolina upset about unfair taxes and local government corruption. In 1768 and September 1770, they stormed downtown protesting their rights. The clock looked on as Royal Governor Lord William Tryon and his militia marched to meet the Regulators at The Battle of Alamance on May 16, 1771. When Tryon’s men defeated the Regulators, this clock witnessed the tragic end of the six Regulators who were tried and executed for rebellion. You can learn more about the War of Regulation in our recent History Trails Adventure: Reckoning with The Regulators.
In the wake of the Regulator War, many Regulators headed west towards the Watauga Settlement near Elizabethton, TN, accompanied by Hillsborough resident James Robertson (later the founder of Nashville, TN). The clock was also keeping watch as Judge Richard Henderson began plans for what would become the Transylvania Purchase, which carved out large swathes of settlement on the western boundaries of North Carolina and present-day eastern Tennessee and Kentucky. While there are no direct records referencing Daniel Boone in Hillsborough, he was contracted by Judge Henderson in surveying what would become ‘Transylvania.’ Learn more about Daniel Boone in North Carolina via the ‘Daniel Boone Trail’
This clock was ticking when the Third Provincial Congress met at St. Matthew’s Church in late August–September 1775. The North Carolina colony worked here to create a provincial government after Royal Governor Martin had effectively been kicked out of North Carolina following the burning of Fort Johnson on July 19, 1775. We attended the 250th anniversary reenactment and living history day of The Third Provincial Congress on the blog—learn more here.
During the Revolutionary War, this clock kept watch as its hours ticked into years. The clock was ticking as The Declaration of Independence was publicly read in 1776, which as signed by future Hillsborough resident, William Hooper...It somberly pasted the hours, when in 1777, the tragic news of the death of Hillsborough’s Francis Nash at Germantown reached his former neighbors.
The clock was ticking as Continental Commander Horatio Gates made his temporary Southern Headquarters in Hillsborough in July–August 1780. Gates had been a hero, along with future turncoat Benedict Arnold, at Saratoga—a victory that earned Gates his leadership role in the south. In studying Saratoga, I learned the two commanders did not get along (each with their egos and strengths). Also after Saratoga, Gates was involved in the Conway Cabal – and while he personally did not try to usurp Washington as commander, some involved in this fiasco did. Learn more here.
North and South Carolina had effectively kicked the British out by 1776 with the Battles of Moore’s Creek Bridge (NC) and Sullivan’s Island (SC), but General Clinton and Cornwallis returned with a vengeance, capturing Charleston in May 1780. On paper, Gates, the hero of Saratoga—the battle that convinced the French to provide full support for the Americans—seemed the man for the job. But as the clock in Hillsborough can tell you, Gates failed miserably.
On August 16, 1780, Gates moved his troops to Camden. They had superior strength, yet Gates’ poor planning led to the worst defeat in American military history based on troop strength. Over 900 Americans were killed or wounded, with countless others taken prisoner by the British. Instead of helping his men, Gates panicked and feverishly raced his horse back from Camden to Hillsborough, where he wrote apologetic letters to General Washington poorly trying to justify his decision.
During the Southern Campaign from 1780–1781, Hillsborough was on edge. The city continued to be a critical supply base for Patriot troops but was now under the threat of retaliation from Loyalist militias. Local Patriots, Thomas Hart and Nathaniel Rochester, who had been involved in Hillsborough’s Third Provincial Congress, fled to Maryland to avoid capture. *Interesting fact – Rochester later founded ‘Rochester NY’!
Meanwhile, Declaration of Independence Signer, William Hooper, fled Wilmington (on the coast) to Hillsborough when the British attacked the port city in 1781. Hooper later settled in Hillsborough, purchasing fellow famed resident and Revolutionary War hero Francis Nash’s house. That historic house still stands on Tryon Street.
The clock ticked on as General Cornwallis stayed in Hillsborough in February 1781, actively recruiting Loyalist militia to fight General Greene in what would become the Battle of Guilford Courthouse (Greensboro) in March 1781.
With Cornwallis in desperate need of supplies after Guilford Courthouse—a pyrrhic victory for the British that ultimately forced them to leave North Carolina—he fled first to Wilmington before meeting his final defeat at Yorktown, VA, on October 19, 1781.
While Cornwallis and his main army had fled North Carolina, local Loyalist militia under the command of David Fanning stormed Hillsborough in a surprise attack on September 12, 1781. Fanning and his men captured North Carolina Governor Thomas Burke, along with 200 militiamen, forcing many of them into British prisons in Charleston area. Burke did eventually escape (4 months later) but he never fully recovered from the ordeal and died in 1783. He is buried at Mars Hill Churchyard just outside of Hillsborough
During this raid, Fanning and his men committed a final act of rebellion by throwing the clock into the Eno River—a deeply ironic fate for a gift originally from King George III. Eventually, the clock was rescued and, after the war, was mounted first on the market house before finally finding its permanent home in 1846 at the Orange County Courthouse, where it continues to stand today.
The clock played witness as Hillsborough hosted the 1788 North Carolina Constitutional Convention—one of several held as the state debated the ratification of the United States Constitution. It formally passed in Fayetteville in November 1789, only after a promise that a Bill of Rights would be added to the document upon ratification.
The clock didn’t stop as the drama of a new century emerged. America building it’s future with hope of liberty, but also the tragedy of slavery that defined plantation life in the region. Hillsborough continued to be a diverse and bustling community, from county seat to industry to conversations between residents as they strolled downtown – the clock ticked on, encouraging them to live in the moment, but also look to the future as time doesn’t stop.
It was during this era that figures like Elizabeth Keckly, a famed African American voice who later became a friend, confidante and seamstress of Mary Todd Lincoln lived and worked in the Burwell School. Today you can tour this historic site, diving into the trials and triumphs of life in Hillsborough in the 1830s-to the edge of The Civil War.
This same clock witnessed the final hours of the United States’ bitter Civil War, ticking as Confederate General Joseph E. Johnston stayed in The Alexander Dickson House. He was preparing to meet General William T. Sherman (Union) to surrender the Southern forces and formally end the war at nearby Bennett Place in neighboring Durham County. *Interesting History – Did you know that after the war Johnston and Sherman became close friends. Johnston worked towards reunification with Sherman. He was even a pallbearer at Sherman’s funeral!
As the Twentieth Century turned the hands of the clock, it remained a constant reminder of time marching on, even through the dark days of World Wars and the Great Depression, and into moments of happy occasions and community nurturing.
The clock helped keep the rhythm as famed jazz and blues musician Billy Strayhorn developed a deep love of music while living in the area with his grandmother and extended family. Today, Hillsborough continues to draw in musicians, with its thriving local scene encompassing sounds from blues and bluegrass to funk, Americana, and beyond.
Today as we near the 250th anniversary of the Signing of the Declaration of Independence, so much has changed across the years, and yet Hillsborough’s clock continues to keep watch. The clock watches over a community that retains its history but is moving toward a brighter future. It’s a place where the arts and education thrive, and music can be heard on the courthouse lawn or in a local bar. The natural beauty of this area, in the shadow of the rolling hills of the ‘Occaneechi Mountains,’ stuns in every season—from spring blooms that could rival a Monet painting, to relaxing days walking the Historic Riverwalk along the Eno, or viewing the fiery fall leaves at Occaneechi Mountain State Park.
The Hillsborough Clock will be looking on, ready to welcome you during your visit to Hillsborough – where you can travel through the past and dig into the stories of centuries of history, or simply enjoy a fall breeze while walking along the Eno River or grabbing lunch or dinner at one of the amazing local eateries like Antonia’s, Saratoga Grill, Wooden Nickel, The Colonial Inn or ‘pig out’ at the Hillsborough BBQ Company…just make sure you save room for dessert at Matthew’s Chocolates, The Town Scoop or Whit’s Frozen Custard.
*I’ll be doing a Hillsborough foodie guide soon*
In the next series of blog posts, we’ll dive deeper into Hillsborough’s history, fun things to do, natural wonders, cool shops, delicious places to eat and area fun…
Don’t forget to subscribe to the blog for the next Hillsborough adventure!
Here are a few resources to help get you started on your Hillsborough adventures
Historic Sites and Museums:
Alexander Dickson House – I mentioned this earlier in the post, but I highly recommend starting your Hillsborough adventure at the Alexander Dickson House. The minute I entered into the home I could feel the history pulsating through the walls. The interior retains its 1790 late Georgian/early Federal design. The house features exhibits about Hillsborough’s history as well as brochures, maps and guides for things to do in the area. Website
Orange County Historical Museum: A wonderful museum in the heart of downtown Hillsborough that tells the story of Hillsborough and Orange County with a variety of exhibits as well as special lectures on a variety of topics from The Regulators to the Music and more. Website
Next door to the museum is the Old Town Cemetery and the Hillsborough Presbyterian Church. This corner of Hillsborough is rich in history. The cemetery has graves dating back to 1757. The church site was originally the home of St. Matthews Anglican Church, which hosted both the Third Provincial Congress and later 1788 Constitutional Convention. St. Matthews was destroyed circa 1800 and later moved to its current location in 1824. The current sanctuary was built in 1814 and given to the Presbyterians after the State made the land and building available to the first religious body in town to call a minister. John Knox Witherspoon became the first minister to accept a call, thus granting the property to the Presbyterian church. The Hillsborough Presbyterian Church remains an active parish in Hillsborough to this day! Read about their church history here.
- Fun fact: Rev. Witherspoon was the grandson of Dr. John Witherspoon, President of Princeton (then College of New Jersey) and the only member of the clergy to sign the Declaration of Independence. John Knox Witherspoon also helped in establishing a church in New Bern as well.
The Colonial Inn – This jewel in Hillsborough has a history dating to 1759 and was recently restored to its former glory. The perfect place to check into history without compromising modern comfort. This is the place to stay while in Hillsborough – they have cozy rooms playing homage to the inn’s dynamic history without sacrificing modern conveniences. They also have an award-winning bar and restaurant. Plan your stay here
Visit Moorefields – you may recall our recent adventure to this hidden historic gem in Hillsborough – built in the 1780s by Supreme Court Justice Alfred Moore, and later the home of intellectual, artist and cat lover, Edward Draper-Savage. Learn about The Moorefields in our recent blog adventure
Ayr Mount – we’ll be touring this soon on American Nomad!
This stunning Federal style home dates to 1815 and was the home of the Kirkland Family for 170 years. Since 1985 it has been owned and restored by Richard H. Jenrette Foundation.
Ayr Mount’s classical architectural design with a two-story central block and flanking single-story wings on either side, became the prototype for many similar houses in North Carolina in coming years. The house is surrounded by 285 acres of picturesque, protected land. For tour information click here
Alliance for Historic Hillsborough is a fantastic organization that works to help protect, restore and share the history Hillsborough. In addition to their preservation work, they provide educational opportunities including self-guided tours to explore Hillsborough’s history. They also hosted guided tours and lectures throughout the year.
Don’t forget to subscribe to American Nomad for the latest adventures
Hi, I’m Adele Lassiter, the travel enthusiast behind American Nomad Traveler. This is where I share my love for history, cool museums, art, and travel tips. When I’m not writing, I’m a singer-songwriter with a passion for Americana music. You can find my new album here: adelelassiter.bandcamp.com
You can also follow us on facebook for the latest blog posts, cool reels, daily history and travel tips
We also have a podcast and vlog – American Nomad Traveler is available on all streaming platforms through Buzzsprout and on YouTube
We are now on Substack for additional content from Travel to History to Art and beyond…
Are you interested in collaborating with American Nomad Traveler…or have an idea for a story? Contact Adele at: americannomadtraveler@gmail.com or use the form below
One thought on “History Trails: Time Traveling in Hillsborough NC”