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Explore Our Properties

Beyond the Tents: Pinehurst’s Year-Round Gathering Places

September 17, 2026

Last weekend, hickory smoke drifted through the Village as Matthew Register of Southern Smoke BBQ and Lewis Donald hosted the Pitmaster Invitational for the Pinehurst Barbecue Festival. For one afternoon, Pinehurst felt like the center of the barbecue world. By Monday, the tents were gone and the Village had settled back into its familiar rhythm. 

Big single-day events draw attention, but they are not what fill a calendar. What does is the kind of recurring experience that returns on schedule, month after month, without needing a headline. Over the past year, Pinehurst has quietly built exactly that.

 At Villaggio, the Italian restaurant inside the historic Magnolia Inn, Thursdays now begin with a 5 p.m. aperitivo hour on the patio. A light drink and bite before dinner may sound small, but that is why it works: it feels less like an event and more like a habit. 

A few blocks away at The Manor, the North & South Bar hosts Third Thursday, a monthly bourbon series with rotating distillery partners, tastings, special releases and guest experts. Because it lands the same week each month, residents can plan around it like a book club or standing tee time. 

The resort has added variations, too, from the Carolina Vista Lounge’s Greens to Glass cocktail class during National Bourbon Month to Bourbon & Bites, which moved to the Carolina Hotel this year and paired whiskey with small plates from five resort restaurants. 

Drum & Quill adds another layer of continuity. This village staple occupies the former Pinehurst Pharmacy, still uses the original drink counter, and honors golf writer Bob Drum, whose work helped define Arnold Palmer’s modern Grand Slam story.

 That same sense of tradition carries through Pinehurst’s America 250 commemoration, with 250 flags at Village Hall, anniversary banners downtown, and a community cookbook, “Stars, Stripes & Shared Traditions,” built from residents’ family recipes and stories.

For anyone thinking beyond the next event and wondering what it takes to live in a neighborhood with this rhythm, The Gentry Team works Pinehurst and the surrounding Sandhills every day. Reach out anytime for a market conversation, no festival required.

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If working with a team that truly gives back to the community matters to you, we would make a great match. Reach out today to get started on buying or selling your home with a team that knows Moore County inside and out. With decades in the industry and an exceptional team of sales specialists, The Gentry Team has sold more homes than any other real estate firm in Moore County—and more than the total volume of most real estate companies in the region. This level of experience is unmatched, allowing us to help you sell your home for top value while anticipating and handling every detail along the way. We work collaboratively, combining our collective expertise to achieve the very best results for our clients. It is an approach built on trust, teamwork, and proven success. When you work with real locals, you get real results.