Unlike the bustling cities to the east, Hillsborough’s location gives it an earnest small-town feel. In the Piedmont region’s oldest town, century-old brick buildings line the cozy downtown streets and relics of the past are sprinkled far and wide. Named “One of the Coolest Small Towns in America” by CNN, this quirky and charming Southern community is filled with farm-focused restaurants, literary creatives, and idyllic outdoor spaces. 

Native Americans inhabited the land millennia before the establishment of Hillsborough in 1754. After European settlement, Hillsborough became an important trading center and even briefly served as the state’s capital during the American Revolution. From historical markers documenting Hillsborough’s early history to Antebellum plantation homes and guided historic tours, Hillsborough’s past is undeniably rich and the community works hard to preserve it. 

Backed by a deep-rooted farming community, Hillsborough has become the center of culinary attention and the epitome of farm-to-table. Just ask Aaron Vandemark, a semifinalist for the James Beard Award for Best Chef: Southeast for his fifth consecutive year and owner of the Italian-influenced restaurant Panciuto, where he estimates 95% of his summer menu is locally-sourced. With the best ingredients and talented chefs, Hillsborough is pioneering the future of food.

Deemed “America’s Little Literary Town” by The Wall Street Journal, Hillsborough is home to more than a dozen top authors like Frances Mayes who wrote “Under the Tuscan Sun” who splits her time between her historic farmhouse in Hillsborough and Tuscany. Be sure to check out Purple Crow Books, a locally-owned bookstore to peruse the local author section or attend one of the regular book signings and author talks. 

Outdoor adventurers flock to the picturesque Eno River State Park, which covers 2,700 acres of land and contains 21 miles of maintained hiking trails. The banks of the Eno River travel beyond the confines of the park to downtown Hillsborough where there’s a paved greenway that winds through parks, playgrounds, and picnic areas. Between the state parks, wooded trails, and grassy fields, Hillsborough has become a popular destination for all things hiking, fishing, swimming, and camping. 

“Hillsborough is a completely unique place,” says Sarah DeGennaro, executive director of the Alliance for Historic Hillsborough. “There is no other town quite like it. It is all at once casual and refined, intellectual and approachable, lively and calm. I love Hillsborough and I love working here.”

I couldn’t agree more. 


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Hillsborough Community Links

Hillsborough Events

Hillsborough Chamber of Commerce

Orange Rural Fire Department

Hillsborough Police Department 

Orange County Planning & Inspections

Town of Hillsborough Government 

Orange County Public Schools

Orange County Public Library

Orange County Arts Commission

Orange County Parks & Facilities

Orange County Sportsplex

Hillsborough Garden Club

Little River Regional Park

Eno River State Park

Schools in Hillsborough

Pathways Elementary
Partnership Academy
Grady A. Brown Elementary
Orange High School
Cameron Park Elementary
C.W. Stanford Middle School
Cedar Ridge High School
A.L. Stanback Middle School
Central Elementary
Hillsborough Elementary


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Masha Halpern - Boutique Real Estate
Keller Williams Realty
101 Cosgrove Avenue, Suite 200
Chapel Hill NC 27514
Direct 919-951-1780
Toll Free 877-478-4669
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Masha Halpern of Keller Williams Realty provides real estate services in the Chapel Hill, Carrboro and Durham, North Carolina area including real estate services for buyer, sellers and those relocating to the surrounding areas of Apex, Bahama,Cary, Efland, Hillsborough, Holly Springs, Mebane, Raleigh, and Wake Forest. Search for homes in Chapel Hill, Carrboro, Durham or the surrounding communities.  Request a market analysis for your North Carolina property.  I list and sell residential real estate, investment property, vacant land, lots for sale in Chapel Hill, Carrboro and Durham, North Carolina area.

Chapel Hill, Carrboro and Durham, North Carolina real estate and homes for sale in North Carolina - Masha Halpern & The Smart Move Team