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cover picture of a historic home on the Hillsborough Guided Walking Tour
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Anna Marie

Stroll Back in Time… Historic Hillsborough Guided Walking Tour

Stroll back in time with PullOverandLetMeOut to enjoy a historic Hillsborough guided walking tour and experience this important North Carolina town that played a pivotal role in American history.
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Hi, I’m Anna Marie. I’m a wife, mother, Irish dancer, and pug mom living in North Carolina. I also love to travel. Come along for the ride! If you see something you like, don’t be afraid to say, ‘Pull over and let me out.’

Hillsborough, North Carolina is a small town that is packed with history. The county seat of Orange County, Hillsborough is situated on the Eno River approximately twenty minutes away from downtown Durham and Chapel Hill. Its scenic beauty and small-town charm make it an attractive destination. However, to fully appreciate and experience this alluring location, a deep dive into Hillsborough’s history is a must. The best method for touring the town and gaining a better understanding of its past is to take a Historic Hillsborough guided walking tour.

The Historic Hillsborough Guided Walking Tour

Established in 1754, Hillsborough is one of North Carolina’s oldest and most historically significant towns. It is imbued with a rich heritage that is still evident today. Each year beginning on Saturdays in March and running through September, it’s possible to stroll back in time and enjoy a historic Hillsborough guided walking tour. Beginning at the visitors center, which is itself a historic building, and continuing from there, this tour provides an outstanding overview of Hillsborough’s incredible legacy.

A historic marker in front of a historic home.
The Alexander Dickson House serves as the Visitors Center

Starting the Tour

Our tour group gathers on the porch of the Alexander Dickson House which serves as the Hillsborough Visitors Center. It is here we meet our guide for the day, Bill, and introduce ourselves to one another.

As we sit in rocking chairs on the porch, Bill gives us a glimpse into Hillsborough’s colonial origins as well as the story of the Alexander Dickson House and how it came to be where it stands today.

The house was built around 1790 and stood about a mile and a half south of town and belonged to a local farmer and businessman named Alexander Dickson. It was used as a temporary headquarters in April 1865 by Generals Wade Hampton and Joseph E. Johnston during negotiations at the end of the Civil War with Union General William T. Sherman.

The time spent on the porch is fascinating. Bill captivates us and keeps us interested with his story as we get ready to start the walking leg of our adventure.

A sign that says Visitors Center
Hillsborough, North Carolina's Visitor Center

Tour Highlights

The tour visits various locations over its several-block route through the old downtown. Bill shares with us stories of the Regulators and their uprising, the Mason Ordinary and Hughes Academy. We also learn of the William Courtney House and see the steps Cornwallis stood on as he spoke to a crowd trying to rally loyalists to join the King’s cause. Likewise, Bill points out the spot where an African-American-owned distillery once stood, providing spirits for the locals.

Moreover, we learn a great deal about the local architecture. From the historic courthouse designed by John Barry and its unique clock to extraordinary homes belonging to community leaders and historic figures to the numerous churches and graveyards and their famous graves, including a signer of the Declaration of Independence.

With each stop along the way, we are treated to a host of fascinating facts and details about the people and events that shaped Hillsborough, North Carolina.

a historic marker in front of an old school house
The Regulator Uprising is an important part of Hillsborough's history.
The Nash-Hooper House, home of William Hooper one of the signers of the Declaration of Independence
a brass plaque with the name Old Town Cemetery on it
Historic Old Town Cemetery

Tips for Taking the Tour

The Historic Hillsborough Guided Walking Tour starts at 10:30 am on Saturdays and the tickets are $10 a person. Tickets may be purchased on the Visit Hillsborough website (be sure to confirm dates and time). You can also check their calendar for other events that may be taking place. The Visitors Center, located at 150 E. King Street, is where the tour begins. There are facilities and plenty of free street parking nearby.

The walking tour travels several blocks of the downtown area. The terrain is pretty level and the walk isn’t strenuous at all. That being said, we did go off pavement and were on grass a couple of times, so comfortable shoes are a must. Likewise, you will want to dress appropriately for the weather as it’s an outdoor tour with only two brief stops inside of the Hughes Academy and Norwood-Jones Law Office.

The tour lasts between 60 and 90 minutes and wraps up in plenty of time to permit additional exploration of the area. You could choose to explore the downtown stores, the museum, the historic Occoneechee Speedway Trailhead, or the popular two-mile Eno Riverwalk greenway.

More History!

For more history, follow up your walking tour with a visit to Ayr Mount. Just outside of the downtown area, this Federal style home belonged to William Kirkland and was built in 1815. Named in honor of his birthplace, Ayr, Scotland, they offer tours Thursdays through Saturdays (check website to confirm).

Ayr Mount is an impressive representation of the Federal style of architecture and the home’s surrounding grounds are equally impressive. I visited a couple of years ago for an event they held at the estate called Outlandish Hillsborough. This delightful Scottish festival is a wonderful celebration of the area’s history, it’s connection to the Outlander series, and the many Scots who traveled here and made Hillsborough their home.

a group of people walking on the street
The walking tour covers several blocks of historic downtown Hillsborough.
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"Hillsborough's downtown historic district — listed on the National Register of Historic Places — features more than 100 homes, churches, schools, and other structures from the late 18th and 19th centuries. Today, Hillsborough is a tourist destination, a haven for artists and writers, and a wonderful place to live. The town is centrally located in North Carolina with fast access to the Triad and other Triangle cities. Interstate 85 runs through the town, and Interstate 40 is just south of its limits."

Dining in Hillsborough

The walking tour wraps up between noon and 12:30 which makes it ideal for planning a post-tour meal.

There are several suitable places on the main thoroughfare from pub dining at the Wooden Nickel to tasty fare at Hillsborough Bakeshop and Pasta Co., and sandwiches and more at the historic Colonial Inn. Additionally, there is Hillsborough BBQ and Eno River Brewing just a few blocks farther out.

a brick building with white columns
The Colonial Inn on King St. serves lunch Mon. through Saturday 11-2, perfect for post-tour dining.

Take Aways

Hillsborough, North Carolina is one of those delightful small southern towns that opens itself up for exploration. I was surprised at how much history there is in this small area. Taking the Historic Hillsborough Guided Walking Tour was an outstanding introduction to the town’s narrative and the important role the area played in North Carolina’s and the country’s history.

Our guide Bill was phenomenal and our friendly crew of tour-takers was a jovial bunch that made our visit all the more enjoyable. This was a pleasant and entertaining tour that delivered a lot of value for the tourist dollar.

Informative, affordable, entertaining, lots of fresh air, sunshine, and scenery- my only regret is that it took me so long to finally take this tour. It is a true Pull Over and Let Me Out gem.

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Our guide Bill was outstanding!

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Stroll back in time...Historic Hillsborough Guided Walking Tour

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