How Southern Pines Stacks Its Holiday Season Onto Back-to-Back Saturdays

If you could only keep one weekend free this December in Southern Pines, which one would it be? The 2026 calendar doesn't let you off that easily. The town's main holiday events fall on three Saturdays in a row, starting Thanksgiving weekend, and each one centers on a short stretch of Broad Street or sits a few blocks from it. Two of those Saturdays have a second event on the same day, and both pairs overlap on paper. On December 5 the shared hour means giving up a real part of one event. On December 12 the overlap is half an hour at the start of a three-hour open house.

November 28: Thanksgiving Saturday on the Sunrise Theater Green

The season opens on Saturday, November 28, two days after Thanksgiving. The Southern Pines Business Association's annual tree lighting takes place in the Sunrise Theater's green space at 250 NW Broad St. Santa arrives by fire truck at 4:30 p.m. and poses for photos until 6 p.m. The organizers ask families to bring their own camera or phone. The tree is lit at 6:15 p.m.

That 6:15 p.m. lighting is the one fixed time on the schedule. The end time varies by listing. The regional visitors bureau shows the event running until 7 p.m., while The Pines Times lists it ending at 6:30 p.m. Either way, the evening has two parts. The Santa line runs from 4:30 to 6, then there's a short gap before the lighting. A family that wants the photo and the lighting is downtown for close to two hours. A household that only wants to see the tree lit can arrive shortly before 6:15.

The same green is the starting point a week later.

December 5: The Morning That Forces a Choice

The Southern Pines Christmas Parade steps off at 11 a.m. on Saturday, December 5. The Southern Pines Business Association and the Town of Southern Pines co-sponsor it, and the 2026 parade application gives it an 11 a.m. to 12:30 p.m. window.

The route explains where people end up watching. The parade starts at the Sunrise Theater, heads south on Broad Street to Massachusetts Avenue, crosses the tracks, comes back north on Broad, and finishes at Connecticut Avenue. Since it runs down Broad and comes back up, much of the downtown sidewalk sees it go by twice.

That same morning, Weymouth Center for the Arts & Humanities hosts Weymouth Wonderland: Wonderfest & Market at 555 E Connecticut Ave., from 10 a.m. to noon. The program is full. It includes the Boyd House decorated for the holidays, a Holiday Shoppe for decor, a Bake Shoppe for treats and warm drinks, Santa, local vendors and artisans, food trucks, and live music and dance.

Compare the two clocks. Weymouth runs 10 to noon. The parade starts at 11. So the two events share a full hour, half of Weymouth's whole program. There are two ways to handle it:

1. Weymouth first, parade second. Get to Weymouth at 10 for the Boyd House and the Bake Shoppe, then head to Broad Street. The parade window runs until 12:30, and the route comes back north toward Connecticut Avenue at the end.
2. Parade first, Weymouth's last hour skipped. Stake out a spot on Broad before 11 and plan on Weymouth's market another year. Wonderland ends at noon, before the parade window closes.

Neither plan gets you all of both. A family that wants Santa can get him on November 28 at the Sunrise Theater green, which takes some of the pressure off December 5. Weymouth also has a Santa visit, so a child can see him at either event.

Pinehurst holds its own events the night before. The visitors bureau lists A Village Christmas and the Village of Pinehurst tree lighting for Friday, December 4. That makes the first weekend of December the busiest stretch of the season.

December 12: A Short Overlap at the Start

A week later, the timing is easier. The Moore County Driving Club calls its Christmas Carriage Parade an annual procession through historic Southern Pines. The club's 2026 calendar has drivers gathering at Gallagher's Field at 11:30 a.m. and leaving the field under police escort at 12:30 p.m. The visitors bureau listing puts the downtown pass at 1 to 1:30 p.m., at 235 NW Broad St.

A half hour is short. A Christmas parade with marching units and floats takes an hour and a half. The carriage parade comes through in thirty minutes, so arriving on time matters more than on December 5.

At 1 p.m., the same time the carriages reach downtown, the Moore County Historical Association opens its annual Christmas Open House. Christmas at the Shaw House runs from 1 to 4 p.m. at 110 W. Morganton Road, and admission is free. The association describes it this way:

"Enjoy old-time decorations, warm apple cider and homemade cookies at the annual Christmas Open House. Tour three house-museums built during the 1700s and 1800s. The event is free to the public to let people see how early Southern Pines and Moore County residents lived."

The two events overlap from 1 to 1:30. The Shaw House open house runs three hours, though, so watching the carriages on Broad first costs only its opening half hour. That leaves 1:30 to 4 for touring all three house museums. The two events are both about horse-drawn travel and old buildings, so the afternoon hangs together.

The Season by the Clock

Here is the full stretch from late October through mid-December, using the times organizers have published.

BooFest is the warm-up. It's listed for Friday, October 23, from 5 to 8 p.m., with trick-or-treating downtown followed by games and crafts at Downtown Park. It's also the only evening on the list held on a Friday.

The Weekdays Between the Saturdays

The Saturdays are spoken for, but the errands that come with the holidays fit into the week. The Moore County Farmers Market is open every Thursday year-round, 9 a.m. to 12:30 p.m., at 604 W. Morganton Road. That's on the same road as the Shaw House at 110 W. Morganton Road.

For cards and gift wrap, downtown has a new shop this year. The Pilot reported that The Paper Trail, a stationery store owned by Alice Gaddis, is fully stocked and open at 110 W. Pennsylvania Ave., part of The Belvedere. According to the paper, it carries notebooks, fountain pens, washi tape, handmade ribbons, art prints, wrapping paper and cards, with many products from England. Gaddis told The Pilot she wants the store to encourage more handwritten letters. It's open 10 a.m. to 5 p.m., Monday through Saturday. That leaves time to stop in before or after the Saturday events.

One store that's been in the local news won't be open in time for the holidays. The Sandhills Sentinel reported on October 7 that The Spice & Tea Exchange is confirmed for Southern Pines, with an opening expected in the first quarter of 2027. That report gave no address or exact date.

If you're thinking about what your Southern Pines home is worth, or want to talk through a move timed around the year ahead, The Gentry Team is happy to help. Request a free market valuation or consultation, and we'll start with what we know about your street.