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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 August in Highland Trails

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

Wednesdays, August 5, 12, 19 & 26, 2026

Hummingbird Banding at Weymouth Woods Sandhills Nature Preserve

Weymouth Woods Sandhills Nature Preserve, 1024 Fort Braggs Rd, Southern Pines, NC • 8:30 AM–~11:00 AM

A unique nature program where residents can observe and learn about Ruby‑throated Hummingbirds through expert-led banding demos—perfect for families or bird‑enthusiasts wanting a hands-on wildlife experience close to home.

Fridays, August 28, 2026

Play Time in the Park (ages 12 & under)

Downtown Park, Southern Pines • 8:00 PM

An evening of giant games, bubbles and family fun in Downtown Park—ideal for Highland Trails families looking for free, active kids’ programming during summer evenings.

Saturdays, August 1, 8, 15, 22 & 29, 2026

Moore County Farmers Market – Saturday Downtown Park

Downtown Park, 156 SE Broad St, Southern Pines, NC • 8:00 AM–12:00 PM (live music 10 AM–noon)

A weekly opportunity for locals to buy fresh seasonal produce, baked goods, and enjoy live music—great for Highland Trails residents to support local vendors and enjoy a vibrant community outing.

Saturday, August 1, 2026

Kid’s Saturday

Village of Pinehurst • 10:00 AM–12:00 PM

A child‑focused morning of fun activities in nearby Pinehurst—easy for Highland Trails families to attend and enjoy creative, hands-on play just a short drive away.

Saturday, August 15, 2026

Classy Trashy Boozy Cruise

Sandhills Trolley departs Red’s Corner, 901 SW Broad St, Southern Pines, NC • 6:00 PM–8:30 PM

A quirky, fun adults‑only trolley outing blending casual and classy styles, offering Highland Trails residents a playful summer social experience in town without needing to venture far.

Thursdays in August 2026

Picnic in the Park – Downtown Park (summer series)

Downtown Park, Southern Pines • 11:00 AM–12:00 PM (e.g., August 12)

Monthly summer gatherings for families to share picnic lunches and social time in Downtown Park—friendly, easygoing mid‑day meetups for neighbors and young children nearby.

From the Neighborhood

Stories, updates, and things to know in Highland Trails

Know Your Neighborhood

Local characteristics and demographics for Highland Trails

Neighborhood Characteristics

Full Guide →

Demographics

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