At 6 p.m. on Saturday, Nov. 21, a 30-foot live tree on the plaza at 500 W. Fifth St. lights up over fire pits, s'mores kits and a brass quintet. Two weeks later, on Dec. 5, the Winston-Salem Ambassadors Holiday Parade comes down Fourth Street, turns onto Liberty Street and ends at Corpening Plaza, where a second downtown tree lights around 6:30 p.m.
Both lightings come at the end of a full day. On each Saturday, the events that take up the afternoon are a few blocks from the tree: a 63-year-old craft fair next door in November, and in December a Moravian market, an art school's holiday sale and Candle Tea. Plan the afternoon around those events and the lighting falls into place at the end.
Nov. 21 runs on one plaza from noon to seven
The Holiday Market & Christmas Tree Lighting at 500 W. 5th is back for its second year, free and open to everyone. The Winston-Salem Journal reported that more than 2,000 people came in 2025 and that organizers want to double that this year. In the same story, Peyton Justice, marketing coordinator at 500 W. 5th, said the hope is "to bring a spirit of togetherness to our building for the market, creating a space that is accessible to all and sparks the joy of the season."
Here is the posted schedule:
- Noon to 7 p.m.: 40+ artisan vendors, food and beer trucks, the s'mores area and a Downtown Grille pop-up
- Noon to 6 p.m.: Free kids' activities on the second floor of the lobby, supported by Kaleideum
- 3 to 7 p.m.: Live music on the plaza
- 6 p.m.: The tree lighting
The music block is bigger than a few carols. The Martha Bassett Show, which plays twice a month at the Reeves Theater in Elkin, is filming its set as "The Martha Bassett Show Holiday Special." The lineup includes The Pharaoh Sisters, DaShawn and Wendy Hickman, Spencer Aubrey, the Piedmont Wind Symphony Brass Quintet, Tiffany Thompson and a local church choir.
The vendor list is posted, so gift shopping can start with a plan. It includes Klim's Gourmet Caramels, Brasstown Chocolate, Goosecreek Pottery, Moravian Mercantile, Sugar Mountain Wreath and Garland, JOLO Winery & Vineyards, Bush Hill Coffee Co. and Las Lobas Fine Jewelry, plus Foothills Brewing, which runs the beer tent. The s'mores are free at the fire pits at the front of the plaza, and any donations go to Crisis Control Ministry and Crossnore.
The fair next door shares the parking
Nov. 21 is also the opening day of the Piedmont Craftsmen's Fair, now in its 63rd year, at the Benton Convention Center. It's a juried fair, with craft artists working in clay, wood, glass, fiber, leather, metal and printmaking. Saturday hours are 10 a.m. to 6 p.m., and Sunday, Nov. 22, runs noon to 5 p.m.
The overlap matters for parking. The streets around 500 W. Fifth close from 11 a.m. to 8 p.m. that day, though the free lots stay open. The building has two free guest lots. One sits between Centenary UMC and 500 W. Fifth, off West Fifth and Poplar Street NW. The other sits between the Benton Convention Center and First Baptist Church, off North Spruce, West Fifth and Marshall. The 4th St. parking deck is also free and open all day.
With the fair running until 6 p.m. right beside one of those lots, the order you do things in decides your day. Start at the fair in the morning, cross to the market after lunch, and stay on the plaza through the 6 p.m. lighting. That way one parking spot covers both events.
The Reynolda Village Holiday Stroll runs the same afternoon from 1 to 5 p.m., with Victorian-costumed carolers, Santa visits and free carriage rides through Reynolda Village. Overflow parking is across Reynolda Road at Reynolda Church. Since the stroll ends at 5, you can do it first and still reach the plaza by 6.
One more detail for Nov. 21: the market and tree lighting are canceled if the weather is bad, and updates go out on 500 W. Fifth's social media pages.
Dec. 5 spreads from Salem Square to Corpening Plaza
The November lighting happens on one plaza. The December lighting comes at the end of a parade, and the day before it is spread over several venues. The same Saturday has Old Salem's St. Nick and the Moravian Market, a regular Candle Tea Saturday at Home Moravian Church, the Sawtooth Holiday Market and a children's play. Put in time order, it looks like this:
- 10 a.m.: Ticketed early shopping opens at the Sawtooth Holiday Market at Sawtooth School for Visual Art.
- 10:30 a.m.: Candle Tea opens at the Single Brothers' House, 600 S. Main St., and runs until 7:30 p.m.
- 11 a.m.: The Sawtooth market opens to everyone, with ceramics, jewelry, textiles, paintings, artist demonstrations and food, for a suggested $5 donation. Theatre Alliance also starts its first Saturday-morning Frosty the Snowman at 650 W. Sixth St., with tickets at $12.
- During the day: St. Nick sits in Old Salem's historic hat shop, and the Wachovia Historical Society holds the Moravian Market in Salem Square, with craft vendors representing the heritage of the Wachovia region.
- 4 p.m.: The Sawtooth market closes.
- 5 to 7 p.m.: The Winston-Salem Ambassadors Holiday Parade heads down Fourth Street and turns onto Liberty Street toward Corpening Plaza.
- About 6:30 p.m.: The tree lighting at Corpening Plaza. Admission is free.
Sawtooth is a block from the parade route, according to Visit Winston-Salem's holiday guide, so the market and the parade fit into one trip. The Sawtooth market closes an hour before the parade starts, which leaves time to find a spot on Fourth Street. Old Salem and Candle Tea are a separate stop. A full Candle Tea tour takes about an hour and 45 minutes, and the house closes at 7:30 p.m., so a tour fits best in the morning or early afternoon, ahead of Sawtooth and the parade.
The two Saturdays side by side
| Saturday, Nov. 21 | Saturday, Dec. 5 | |
|---|---|---|
| Tree | 30-foot live tree at 500 W. Fifth St. | Corpening Plaza, at the end of the parade |
| Lighting time | 6 p.m. | About 6:30 p.m. |
| Event hours | Market noon to 7 p.m. | Parade 5 to 7 p.m. |
| Cost | Free | Free |
| Also that day | Piedmont Craftsmen's Fair at Benton, 10 a.m. to 6 p.m.; Reynolda Village Holiday Stroll, 1 to 5 p.m. | Sawtooth Holiday Market, 11 a.m. to 4 p.m.; St. Nick and the Moravian Market in Old Salem; Candle Tea, 10:30 a.m. to 7:30 p.m. |
| Getting there | Roads around 500 W. Fifth closed 11 a.m. to 8 p.m.; free guest lots and free 4th St. deck | Route runs along Fourth and Liberty streets |
Dec. 5 has events in other towns too. Kernersville's Hometown Christmas runs 4 to 8 p.m. that evening, with free trolley rides and the town tree lighting from 7 to 8 p.m. That's also the first night of Christmas by Candlelight at Körner's Folly, where advance tickets are recommended because the event typically sells out. Households that split up across the Triad that night will have to choose.
What to book before Thanksgiving
Most of these events are free and need no tickets. A few do need planning, and the Dec. 5 plan depends on them.
Candle Tea. Home Moravian Church says reservations are highly recommended because tickets sell out, though walk-ups are taken as space allows and may have a short wait. The full tour lasts about an hour and 45 minutes. It includes carol singing in the Saal with the 1787 pipe organ, a candle-making demonstration, coffee and sugar cake in the historic kitchen, the Putz and the Nativity. Admission is $9, $5 for children 3 to 12, and free for children under 3. The church notes that the Single Brothers' House is not handicapped accessible. It has steps at both entrances and three steep flights of stairs inside, and strollers stay in the entrance room. If Dec. 5 is already full, the other regular Saturday is Dec. 12, from 11:30 a.m. to 7:30 p.m. That's the same day as ChristmasFest, which runs 10 a.m. to 5 p.m. at Salem College's Elberson Fine Arts Center and the Archie K. Davis Center.
Old Salem admission. The St. Nick and Moravian Market activities come with general admission. Holiday admission tickets are sold online starting Nov. 11, and Old Salem says tickets for these special dates don't need to be bought in advance and don't sell out. You can buy them on-site at the Visitor Center, Winkler Bakery or MESDA. Candle Tea is separate from Old Salem's own tours, and the two use different drop-off spots.
Joy of Christmas. Old Salem's evening walking tours run Fridays and Saturdays from Nov. 27 to Dec. 19, departing every 15 minutes from 6:30 to 7:45 p.m. They need separate tickets. Because those times overlap the 6:30 Corpening Plaza lighting, a Dec. 5 tour means skipping the parade's finish.
For more about life in the city between holiday weekends, our Winston-Salem neighborhood page covers the rest of the year.
At The Jordan Factor, we plan around timelines for a living, and these two Saturdays reward the same approach: pick your parking, put the afternoon events in order, and get to the tree on time. If you're thinking about a move or a sale in Winston-Salem and want that kind of planning on your side, Let's Connect.
