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Hillsborough

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One of the coolest small towns in America

Population: 6,381+
County: Orange County 

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About Hillsborough

Hillsborough is the oldest town in the Triangle area. Located about 15 minutes northwest of Chapel Hill in Orange County, the quaint town claimed national spotlight as CNN recognized it as the third “Coolest Small Town in America” and Budget Travel Magazine’s readers voted it into the top 15 “Coolest Small Towns 2015.”  

Not surprisingly, it has recently seen unprecedented growth with new homes, townhouses, condominiums and apartments on the way.

Featured Hillsborough Listings

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Things To Do in Hillsborough

Downtown Hillsborough

Its small town charm has captured the attention of North Carolina artists and writers for many, many years, so much so that the Wall Street Journal dubbed it “America’s Little Literary Town” due to the numerous writers in residence. A stroll through its colonial-style downtown unveils a mix of local restaurants, coffee shops, galleries and boutiques. West Nash Street is also a favorite frequent among residents who describe it as a great place to spend a lazy Saturday sipping on local craft beer from The Mystery Brewery Public House and enjoying a barbeque plate from Hillsborough BBQ Company.

Downtown Hillsborough comes alive on the last Friday of every month as the Hillsborough Art Council hosts an Art Walk event filled with gallery showcases, art exhibits, wine tastings and more. Every Saturday the Eno River Farmers Market opens on the northwest corner of Court House Square with fresh vegetables and fruits, local meats and cheeses and artisanal offerings.  

Outdoor Activities

Hillsborough residents and visitors enjoy the town’s numerous parks, greenways and recreation centers. Its new Riverwalk paved urban trail winds 1.8 miles along the Eno River connecting various parts of the growing community. It is the first section of the N.C. Mountains-to-Sea Trail to run through Orange County. The 2,700-acre Eno River State Park also touches the town offering a vast wilderness escape with camping, hiking and rafting activities. 

Hillsborough's Top Picks

Eno Gallery

A contemporary fine art gallery in the heart of Hillsborough’s historic district. Eno features monthly solo and selected group shows

Occoneechee Speedway

Shut down in 1968 after Richard Petty’s win, this speedway was placed on the National Register of Historic Places and has over 3 miles of walking trails.

Alexander Dickson House

This Hillsborough visitor's center, which is a 1769 Quacker-plan farmhouse, is in the heart of this historic town.

Close Proximity to RTP

Located between Interstate 85 and Highway 70, Hillsborough has become a favorite residence for families with personal and professional ties in Chapel Hill, Durham, Raleigh and the Research Triangle Park. 

Locals consider Hillsborough a great North Carolina treasure and you will too. 

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