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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 September in Highland Trails

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

September 5–6, 2026

Pinehurst Barbecue Festival

Village of Pinehurst / Pinehurst Fair Barn / Moore County Airport • Fri 6:00 PM–8:30 PM; Sat 11:00 AM–1:00 PM & 5:00 PM–7:00 PM; Sun from 11:00 AM

This popular three‑day barbecue celebration in nearby Pinehurst features pitmaster dinners, grilling classes, bourbon tastings, and a Pitmaster Invitational—perfect for food lovers living in Highland Trails.

Throughout September 2026 (weekly Thursdays & Saturdays)

Moore County Farmers Market

Armory Sports Complex (Thursdays) & Downtown Park Southern Pines (Saturdays) • Thursdays 9:00 AM–12:30 PM; Saturdays 8:00 AM–12:00 PM

A convenient local source of fresh seasonal produce, baked goods, and crafts—just minutes away from Highland Trails—with live music Saturdays through October.

September 11, 2026

Pinehurst Live After 5

Village of Pinehurst • 5:15 PM–9:00 PM

An early‑evening concert series in Pinehurst offering live music and community atmosphere—an easy and enjoyable outing for residents of Highland Trails.

September 25, 2026

Phil Vassar – Sandhills Celebrates America’s 250th: Sunrise Theater Concert

Sunrise Theater, Southern Pines • 7:00 PM–9:00 PM

Country star Phil Vassar performs live downtown as part of the America’s 250th celebration—great local entertainment that’s walkable or a quick drive from Highland Trails.

September 26, 2026

Sandhills Celebrates America’s 250th Celebration Concert – Dustin Lynch

Gilliam‑McConnell Airfield, Carthage • 6:00 PM–10:00 PM

A full evening of patriotism, music headlined by Dustin Lynch, aerial shows, and drone displays—worth a short drive for a festive night out.

September 27, 2026

Hello Autumn Farm Festival 2026

Kalawi Farm, Eagle Springs • 10:00 AM–7:00 PM

A charming fall festival with corn maze, hayrides, pumpkin patch, and play areas—ideal for families in Highland Trails seeking seasonal fun just a short drive away.

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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