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Southern Pines

Highland Trails, Southern Pines Neighborhood

Nestled among towering pines, Highland Trails is a welcoming neighborhood known for its spacious lots, classic ranch-style homes, and tranquil, winding roads. With a friendly, close-knit community and easy access to nature trails, it’s the perfect place to enjoy Southern comfort and a peaceful, neighborly atmosphere.

Southern Pines, North Carolina, in Moore County offers a peaceful and tranquil atmosphere surrounded by quiet streets and calm neighborhood surroundings. The community features a variety of housing options, including newer single detached homes as well as charming small apartment buildings and duplexes. Primary schools are conveniently located near most residences, providing easy access to education. A selection of public and private elementary schools enhances educational choices. Daily errands are supported by scattered pharmacies selling essential items and several local restaurants provide diverse dining options. The area’s gentle slopes and limited cycling paths offer moderate outdoor activity opportunities within a mostly relaxed setting.

People who prefer a slower-paced ambience will enjoy Southern Pines. Southern Pines is very good for those who like quiet surroundings, as the streets are generally very calm.

Highlights of Highland Trails

Parks, schools, dining, and what makes this neighborhood special

🌳 Community Lake & Walking Trails

A serene lake nestled within the Highland Trails neighborhood, surrounded by pleasant walking and hiking paths maintained by the HOA, offering residents easy access to nature and outdoor activity right at their doorstep.

🏘️ Highland Trails Residents Association

The active Residents Association organizes seasonal social events like Easter, Halloween, and Oktoberfest, fostering a tight‑knit, community‑oriented atmosphere unique to Highland Trails.

🏫 Moore County Schools (Southern Pines Elementary, Southern Middle & Pinecrest High)

Families in Highland Trails are served by nearby Moore County public schools including Southern Pines Elementary, Southern Middle, and Pinecrest High, all within short commuting distance and important to local life.

🍽️ Filly & Colts at Longleaf (Neighborhood Favorite)

A beloved local spot frequently praised by Highland Trails residents for its superb homemade soups, chili, and baked goods, often highlighted in community recommendations as a neighborhood favorite.

🚶 Tree‑Lined Streets & Walkability

The neighborhood is characterized by its peaceful, family‑friendly environment filled with mature, shaded tree‑lined streets that encourage walking and reflect its walkable, tranquil charm.

A Southern Pines Neighborhood

This October in Highland Trails

Things to do, events, and what's happening this month

October 3, 2026

AutumnFest

Downtown Park • 9:00 AM–4:00 PM

This annual downtown Southern Pines festival is an easy outing from Highland Trails, featuring more than 100 arts, crafts, and food vendors plus live entertainment. Residents can browse handmade goods, enjoy lunch outdoors, and make a full family day of the town’s signature fall celebration.

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October 10–31, 2026

Moore County Farmers Market — Saturday Markets

Downtown Park • 8:00 AM–12:00 PM

The Saturday market offers a convenient way for Highland Trails residents to shop for locally grown produce, baked goods, eggs, and handmade products close to home. Live music is scheduled from 10:00 AM to noon when weather permits, creating a relaxed weekend activity in downtown Southern Pines.

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October 8, 2026

Coming Home: The Music of James Taylor — Featuring James Gedeon

Owens Auditorium at Bradshaw Performing Arts Center • 7:00 PM–8:15 PM

This intimate acoustic tribute in nearby Pinehurst gives Southern Pines residents an appealing evening concert option without traveling far. James Gedeon performs well-known James Taylor songs in a close-up setting, making it suitable for a relaxed date night, friends’ outing, or music-focused regional evening.

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October 11, 2026

Second Sunday at Weymouth Center — Pop Up in the Pines

Weymouth Center • 11:00 AM–4:00 PM

This free Southern Pines pop-up combines local vendors, food trucks, drinks, and live music in the scenic Weymouth Center setting. It is a nearby, low-pressure Sunday activity for Highland Trails residents who want to browse local makers, enjoy the grounds, and support small businesses.

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October 23, 2026

Halloween Costume Party and BooFest

Southern Pines Public Library and Downtown Park • 3:30 PM–8:00 PM

Families from Highland Trails can begin with music, dancing, and Halloween activities at the library, then continue downtown for BooFest’s trick-or-treating, carnival games, prizes, and spooky entertainment. The closely timed events create an especially convenient, festive afternoon and evening for children and caregivers.

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From the Neighborhood

Stories, updates, and things to know in Highland Trails

Know Your Neighborhood

Local characteristics and demographics for Highland Trails

Neighborhood Characteristics

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Demographics

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