A Season to Savor: Your Guide to Holiday Events, Local Shopping & Winter Magic in Pinehurst 

The holiday season in Pinehurst brings a welcome mix of festive energy, small-town charm, and community traditions. From Thanksgiving through New Year’s, Forest Creek, the Village, and surrounding Sandhills come alive with markets, musical performances, family activities, and plenty of ways to shop local. Whether you’re hosting out-of-town guests, planning outings with kids, or simply looking for holiday inspiration close to home, Pinehurst offers something for everyone this time of year. 

Here’s your curated guide to the best holiday happenings, festive outings, and winter experiences throughout the Forest Creek area and beyond. 

Thanksgiving Weekend & Early Holiday Shopping 

Thanksgiving in Pinehurst often sets the tone for the entire season—crisp mornings, perfect golf weather, and the gentle glow of holiday lights beginning to appear throughout the Village. 

Shop Small This Season: November 24–29 

The Village of Pinehurst invites residents and visitors to celebrate the holidays by supporting local shops, restaurants, and service providers. From November 24–29, anyone who shops, dines, or receives services from a local business can bring their receipt to the Pinehurst Welcome Center to enter daily drawings for beautifully curated gift baskets donated by merchants. It’s an easy, festive way to support small businesses while knocking out early holiday shopping. 

Pop-Up Holiday Market at The Fair Barn: November 29 

On November 29, the Pop-Up Holiday Market at The Fair Barn features over 35 vendors, holiday displays, and food trucks. It’s one of the best places to find unique gifts, handmade goods, local treats, and festive décor—all under one roof. Whether you’re shopping for neighbors, colleagues, or family, this market makes it easy to discover something special. 

Local Shops to Visit 

Beyond the markets, Pinehurst and Southern Pines offer plenty of specialty shops perfect for thoughtful holiday gifts. Cooper & Bailey’s Boutique stocks elegant apparel and curated home goods, while The Pinehurst Olive Oil Company and Southern Whey offer gourmet flavors ideal for hosts, food lovers, and charcuterie enthusiasts. And for those who love nothing more than curling up with a great book when the temperatures drop, The Country Bookshop is a cozy, charming stop—full of giftable reads, local authors, and seasonal titles. 

Holiday Events & Community Traditions 

Throughout November and December, Pinehurst fills its calendar with holiday events ranging from family-friendly activities to refined seasonal performances. 

Festival of Trees: Adopt-a-Holiday Pal — November 20 

Perfect for families with young children, this event invites kids to “adopt” a plush moose or bear, decorate a festive gift bag, and receive an official adoption certificate—all while surrounded by beautifully decorated trees. Parents can capture photos, sip cocoa, and enjoy watching little ones embrace the magic of the season. All proceeds support Sandhills Children’s Center, making it an especially heartwarming outing. 

TEAM WORKZ Christmas Toy Drive & Holiday Market — November 22 

Held at Cox’s Double Eagle Harley-Davidson—proof that holiday cheer pops up in the most unexpected places—this lively event blends giving back with festive fun. Families can take selfies with Santa, Mrs. Claus, and even The Grinch while browsing local artisan vendors and enjoying bites from the Tanglewood Farms Food Truck. Guests are encouraged to bring a new, unwrapped toy to benefit local families, making this event as meaningful as it is cheerful. It’s a great stop for out-of-town visitors wanting to experience the playful, community-driven side of the Sandhills. 

Festive in Flight: Holiday Drone Show — November 28 

Pinehurst Resort’s “Festive in Flight” transforms The Cradle into a stunning holiday spectacle. Hundreds of synchronized drones paint the night sky with festive scenes choreographed to holiday music. Before the show begins, families can enjoy visits with Santa, Neon Glow Putting, stilt walkers, food and beverage offerings, and live DJ entertainment. Bring your own chairs and settle in—it’s one of the season’s most dazzling outdoor experiences. 

Christkindlmarkt — November 30 

This youth-driven German-style Christmas market at Cannon Park is as charming as it is unique. Fifteen young entrepreneurs set up shop with handmade crafts, treats, artwork, and holiday décor. Guests can enjoy hot cocoa, free raffles, a gift-wrapping station, and live music performed hourly by local youth. It’s festive, family-friendly, and a wonderful way to support the next generation of makers. 

A Very Pinehurst December 

December brings some of the most beloved traditions of the season—classic events that fill the Village with warmth, music, lights, and community spirit. 
 
Members don’t have to go far to enjoy a bit of holiday magic. Forest Creek has two festive traditions of our own this season. On Friday, December 5th, the Holiday Shopping Experience at the Golf Shop (2:00–7:00pm) features wine, cheese, exclusive in-store discounts, and onsite favorites like William & Harry and Fine Tuned—perfect for checking off a few gift-list items in a relaxed, seasonal atmosphere. Then on Sunday, December 7th, the Club hosts the always-popular Brunch with Santa, complete with a kid-friendly buffet, holiday crafts, ornament making, and plenty of photo opportunities with Santa and his Elf. It’s a warm, family-focused event and a wonderful way to make memories right here at home. 

A Village Christmas Holiday Open House — December 5 

From 4pm–7pm, downtown Pinehurst transforms into a festive, walkable holiday scene with extended shop hours, pop-ups, and seasonal displays. It’s an easy, relaxing outing—perfect for browsing with friends, enjoying a holiday date night, or entertaining guests visiting for the weekend. 

Pinehurst Christmas Tree Lighting — December 5 

Immediately following the Open House, the annual Christmas Tree Lighting at Tufts Memorial Park begins at 6:30pm. This cherished tradition features choirs, entertainment, a street market, and plenty of seasonal cheer. Families, neighbors, and visitors gather to watch the Village sparkle to life—a moment that truly feels like the start of Christmas in Pinehurst. 

Carolina Cookie Exchange — December 7 

Held at The Village Pine Venue, this beloved community gathering invites participants to bake four dozen cookies and exchange them for three dozen assorted treats. Guests can enjoy tastings, a seasonal drink, a charcuterie grazing table, hors d’oeuvres, and a full hot cocoa bar. Prizes are awarded for Best Decorated and Most Delicious, making it a joyful, cozy event for bakers, families, and cookie lovers. 

North Carolina Symphony “Holiday POPS!” — December 10 

For a refined holiday outing, the North Carolina Symphony’s “Holiday POPS!” concert at Owens Auditorium delivers an evening of classic carols and seasonal favorites. Conducted by Sophie Mok, this annual performance is a beautiful tradition that appeals to audiences of all ages. 

Breakfast with Santa — December 13 

Held in the historic Sandhills Woman’s Exchange cabin, this event is ideal for young families. Kids enjoy breakfast, a magic show, face painting, balloon animals, and holiday music—before visiting Santa himself. Parents should bring their cameras; the rustic cabin backdrop makes for wonderful holiday photos. 

Quiet Winter Moments & Seasonal Sips 

Standardbred Training at the Pinehurst Harness Track 

From October to April, visitors can stop by the historic Harness Track between 7am and 1pm to watch Standardbred horses during winter training. It’s peaceful, scenic, and a wonderful early-morning activity for guests or families looking for something unique to Pinehurst. 

The Village Wine Shop Tastings 

Throughout the season, The Village Wine Shop hosts tastings featuring reds, whites, sparklings, and seasonal favorites. Their knowledgeable team helps guests pick the perfect bottles for gifting, hosting, or enjoying by the fire. 

Holiday Shopping, Pinehurst Style 

Beyond the events, the area’s boutiques and specialty shops offer endless options for holiday gifting. Daphne’s Hallmark Shop carries ornaments, holiday cards, and décor; The Pinehurst Olive Oil Company and Southern Whey offer gourmet treats and artisan foods; Cooper & Bailey’s Boutique stocks elegant apparel and homewares; and The Spa at Pinehurst offers giftable experiences perfect for a relaxing winter reset. 

A Season of Community, Celebration & Small Moments 

Whether you’re selecting gifts from local shops, attending one of the Village’s signature events, or simply enjoying a winter morning beneath the pines, the holiday season in Pinehurst is full of ways to slow down and savor the moment. From Thanksgiving through New Year’s, may your season be filled with warmth, community, and the timeless charm that makes this area so special.