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Before and after: See how much Hillsborough St. has changed with these interactive photo sliders

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Howling over Hillsborough

More than any place in Raleigh, Hillsborough Street flaunted the city’s playful character and scruffy charm. Now, it’s mourned, lamented and dismissed by the city’s more-seasoned locals — defined, most often, by landmarks it has lost. Though some look to the future and embrace change, others reject modernity. Dive into nostalgia with this special report.


It’s been more than 150 years since Hillsborough Street was first established in Raleigh. The road was originally named Hillsboro Street (or Road) because it took travelers to the small town of Hillsboro in Orange County. In 1965 the General Assembly officially changed the spelling to Hillsborough, in part to match the renaming of the town.

Using archival images from The News & Observer’s files, along with photos from the Albert Barden and W. W. “Bud” White Southern Bell Photograph Collections at the State Archives of North Carolina, we’ve created these interactive graphics to show how much has changed over the last 100 years.

Beginning downtown, here are landmarks along the way to the fairgrounds. Click or touch the center circle of each image and move it left and right to reveal the full photo.

Hillsborough at West Street

Now the site of the 20-story 400H tower under construction, the corner of Hillsborough and West Streets was Martin’s Paramount Service Station in the mid-1930s before becoming an A&P Supermarket in 1938. That building burned down in 1952.

Char-Grill

The Char-Grill still remains (for now) in the 700 block of Hillsborough Street, but just about everything else has changed in the last 60 years.

The old Darryl’s corner at Oberlin Road

Home of the much-loved Darryl’s Restaurant which opened at the corner of Hillsborough and Oberlin in the 1980s, the building remains remarkably unchanged 40 years later. It now is home to David’s Dumpling and Noodle Bar.

NC State’s belltower

Originally constructed to honor N.C. State alumni killed in World War I, the cornerstone for the Memorial Belltower at Hillsborough Street and Pullen Road was laid in 1921. But with the Great Depression and World War II the monument was not formally dedicated until 1949.

Sadlack’s at Enterprise Street

Sadlack’s Heroes, at the corner of Hillsborough and Enterprise Streets, was a well-known Raleigh hangout for decades. It gave way to new development that now includes an Aloft Hotel and Gonza Tacos y Tequila restaurant.

Once a bowling alley and movie theater

N.C. State students and fans celebrate the Wolfpack’s win over UNLV in the 1983 NCAA men’s basketball tournament on the stretch alongside main campus. This part of Hillsborough has been completely reformed.

Apartment, CVS replace old bar, restaurant

Time Out restaurant and Katmandu bar in the 3100 block of Hillsborough Street now is a CVS Pharmacy and the Stanhope Apartments.

That iconic tractor sign

The iconic tractor sign stood atop the North Carolina Equipment Company Building on Hillsborough Street for more than 80 years. The building was demolished in 2018, but developers saved the sign, which now sits on The Standard of Raleigh, off-campus apartments for N.C. State students.

The Wilmont

Built in 1926 along the stretch of Hillsborough Street just before Meredith College, The Wilmont is a registered historic landmark. It features 24 apartments that preserve the vintage architecture while offering modern amenities.

This story was originally published August 31, 2022 at 6:00 AM with the headline "Before and after: See how much Hillsborough St. has changed with these interactive photo sliders."

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Howling over Hillsborough

More than any place in Raleigh, Hillsborough Street flaunted the city’s playful character and scruffy charm. Now, it’s mourned, lamented and dismissed by the city’s more-seasoned locals — defined, most often, by landmarks it has lost. Though some look to the future and embrace change, others reject modernity. Dive into nostalgia with this special report.