If you could keep only one Saturday open between Thanksgiving and Christmas this year in Southern Pines, which would it be? The 2026 calendar points to December 5. That morning the Southern Pines Business Association's Christmas Parade starts on Broad Street at 11 a.m., and Weymouth Wonderland and Holiday Market has already been open on the Weymouth lawn for an hour.
Most of the season works this way. Events don't spread evenly across six weeks. They bunch up around a few weekends, and some share a day. Planning by weekend, with the dates below, makes it easier to see where two things fit in one outing and where they compete for the same hours.
Thanksgiving Weekend Starts Before Breakfast
The season begins on Thanksgiving morning, Thursday, November 26, well before the turkey goes in. The Moore County Hounds hold their Opening Meet and Blessing of the Hounds at Cameron's Meadow–Buchan Field, 225 Mile Away Farm Lane, from 7 a.m. to noon. The Pines Times event listing says the tradition goes back more than 100 years in Southern Pines and draws more than 1,000 spectators. The nonprofit Preserve the Sandhills hosts it.
Plan your morning around three details:
- The blessing starts promptly at 10 a.m. The listing says to allow at least an hour to park and walk from Lyell's Meadow to Buchan Field.
- Leave the family dog at home. Dogs and pets are not allowed.
- Front tailgate spots are limited. VIP tailgating is handled directly through Moore County Hounds.
The body text of that listing still says "Thursday, November 27th," which matches last year's Thanksgiving. The event's calendar entry gives November 26, and that is Thanksgiving Day in 2026.
Two days later, the weekend moves downtown. The SPBA's annual tree lighting is Saturday, November 28, on the Sunrise Theater's green space. Santa arrives by fire truck at 4:30 p.m. and poses for photos until 6 p.m. Bring your own camera or phone. The tree is lit at 6:15 p.m., and the event is free. The SPBA's tree lighting page has the same schedule.
That leaves about an hour and three-quarters between the start of Santa photos and the lighting. If your Saturday errands include wrapping paper or cards, The Paper Trail is a short stop on the same afternoon. It's a new stationery and gift shop at 110 W. Pennsylvania Ave. in The Belvedere, owned by Alice Gaddis. The Pilot reported that it carries notebooks, fountain pens, stickers, washi tape, handmade ribbons, art prints, wrapping paper, cards and desk lamps. According to The Pilot's business coverage, the store was fully stocked and open by late September.
December 4 and 5 Is the Busiest Stretch
The first weekend of December has the most going on in the shortest time, and much of it centers on Connecticut Avenue.
It starts Friday night, December 4, at 6 p.m. with Candlelight & Carols in the Great Room of the Boyd House at Weymouth Center. The Women of Weymouth host it as the kickoff to Weymouth's holiday celebration. It's an adults-only evening with a caroling sing-along, a signature drink, passed appetizers and desserts, and guests are asked to wear festive attire. Tickets are sold through the Weymouth Center calendar.
Saturday has two events on one morning. Here is how they line up:
- 10 a.m. Weymouth Wonderland and Holiday Market opens on the Weymouth Center lawn at 555 E. Connecticut Ave. and runs until 4 p.m. No ticket is needed, and donations are appreciated.
- 11 a.m. The SPBA Christmas Parade leaves the Sunrise Theater. It goes south on Broad Street to Massachusetts Avenue, crosses the tracks, comes back north along Broad Street, and ends at Connecticut Avenue.
- Afternoon. Weymouth stays open until 4 p.m., so there is time to go after the parade.
The parade ends at Connecticut Avenue, and Weymouth's address is on East Connecticut Avenue. You could go to the market first or after the parade, and either way you can see both in one day. The SPBA parade page lists high school marching bands, dance teams, floats from local organizations and Moore County businesses, fire trucks, antique cars, Misses and Princesses, and Santa Claus.
Weymouth Wonderland fills the rest of the day. Pop Up in the Pines hosts the Holiday Market. Visitors can tour the Boyd House decorated for the season, shop for decor in the Holiday Shop, get a warm drink and a treat at the Bake Shop, visit Santa, browse local vendors and artisans, eat from area food trucks, and listen to local performers.
Santa is at both events, so families who want a photo may only need one line.
December 12 Has Afternoon History and a Night Show
The second Saturday in December brings two very different events.
From 1 to 4 p.m., the Moore County Historical Association opens the Shaw House at 110 W. Morganton Road for Christmas at the Shaw House. Admission is free. MCHA members have their own Holiday Party at the same house two days earlier, Thursday, December 10, from 5 to 7 p.m. Dates and details are on the MCHA events page.
The same day, the Sunrise Theater presents Good Shot Judy & the Satin Dollz Holiday Extravaganza at 3 p.m. and 7:30 p.m. Listed prices run from $26.15 to $153.65. The 3 p.m. show starts during the Shaw House open house, so if you want both, the 7:30 p.m. show leaves room for the afternoon.
The Week Before Christmas Belongs to the Sunrise
By mid-December, most of the action moves indoors to the Sunrise Theater on Broad Street, the same green space where the tree was lit three weeks earlier.
| Date | Event at the Sunrise Theater | Times | Cost |
|---|---|---|---|
| Friday, Dec. 18 | The Polar Express | 7 p.m. | Free, no ticket required |
| Saturday, Dec. 19 | The Murphy Family Christmas Holiday Concert | 3 p.m. and 7 p.m. | See listing |
The Friday screening is the only Sunrise holiday event on this list with no ticket at all. It falls on the last weekend before Christmas, when many families have kids home and relatives visiting. Times and prices for both are on the Sunrise Theater's ticketing page.
Smaller Dates Earlier in November
A few November events help get things ready before the big weekends.
- Wednesday, Nov. 4, 11 a.m. The Women of Weymouth November meeting in the Great Room features a holiday fashion show by Monkee's of the Pines. Registration and a lunch reservation go through Weymouth's calendar.
- Tuesday, Nov. 10, 3:30 to 4:30 p.m. The Southern Pines Public Library's Correspondence Club writes Santa letters and holiday cards. It's on the Town of Southern Pines calendar.
- Sunday, Nov. 22, 2 p.m. At Weymouth's Chamber Sessions, The TrebleMakers, young string players from the Carolina Philharmonic Junior Orchestra program, perform in the Great Room. The program draws on the history of the Boyd House and James and Katharine Boyd.
One date to watch for is the SPBA's Claus-mopolitan Crawl, a downtown shop-and-sip with holiday discounts. Its 2026 page says the date is "coming SOON!" so check the SPBA event page before planning around it. These listings come from organizer and ticketing pages, and schedules can change. Confirm times and prices with each host before you go.
The Season on One Page
| Weekend | Main events | Where |
|---|---|---|
| Nov. 26 to 28 | Blessing of the Hounds, Thursday 10 a.m.; tree lighting, Saturday 6:15 p.m. | Buchan Field; Sunrise Theater green space |
| Dec. 4 to 5 | Candlelight & Carols, Friday 6 p.m.; Weymouth Wonderland 10 a.m. to 4 p.m. and parade 11 a.m., Saturday | Weymouth Center; Broad Street to Connecticut Avenue |
| Dec. 10 to 12 | MCHA members' party, Thursday; Christmas at the Shaw House 1 to 4 p.m. and Sunrise Holiday Extravaganza, Saturday | Shaw House; Sunrise Theater |
| Dec. 18 to 19 | The Polar Express, Friday 7 p.m.; Murphy Family concert, Saturday | Sunrise Theater |
Of the four weekends, December 5 is the only one where two major events share a morning and end up on the same avenue.
Hosting family for the holidays, or getting a vacation rental ready for guests who come to Southern Pines for the parade and the hounds? Meese Property Group is based in Southern Pines and can help you plan around these weekends, from timing a guest stay to setting a short-term rental's calendar. Request a personalized consultation and we'll go through your December with you.
