Old Town Greenwood's Holiday Open House started as a shopping punch card. In recent years, pieces have been added on top of it. A parade came first, then a tree lighting, then a city drone show. The 2026 version runs Friday, Nov. 20, and Saturday, Nov. 21. It lands in a downtown where the next addition is already going up on Surina Way. That addition is a $7.5 million plaza whose plans include a seasonal ice rink.
That growth explains the shape of the season, so it comes first.
How a Punch Card Became a Parade Night
The open house is run by Discover Old Town Greenwood, the volunteer group behind the downtown's festival calendar. Its purpose has always been commercial in the best sense. "We want to do something for the business community to bring people into those businesses," Scott Eanes, the group's president, told the Daily Journal last November. "The Holiday Open House was developed from that, with the punch card, so people get to visit at least the local businesses on that card."
The same Daily Journal story laid out how the weekend grew. It shows a pattern of small, deliberate additions rather than one big relaunch.
| Stage | What was added | Who added it |
|---|---|---|
| The original event, more than a decade ago | Shopping open house with a prize punch card | Discover Old Town Greenwood |
| 2023 season | Girls' Night Out, a lighted parade around Old Town, tree lighting at Folktale Greenwood | Discover Old Town Greenwood |
| 2025 season | First holiday drone show | Greenwood Parks and Recreation |
| 2026 season | Tree lighting listed at Greenwood City Center | Discover Old Town Greenwood schedule |
The 2025 drone show marks the moment the city stepped in. Rob Taggart, Greenwood's parks and recreation director, told the Daily Journal that the idea grew out of the Freedom Fest drone show. "The city really wanted to get behind and support what (Discover Old Town Greenwood) is doing," he said. Eanes called it "a whole Old Town event that keeps growing and growing naturally."
Folktale Greenwood, the event venue in the historic home at 243 S. Madison Ave., hosted that tree lighting for the past few years. For 2026, Discover Old Town Greenwood lists the tree lighting at Greenwood City Center. The city's own drone show page still shows last year's details, with a Nov. 22 date and the Folktale lighting. If you are planning around the tree lighting, go by the organizer's 2026 listing.
Saturday, Nov. 21, Hour by Hour
Friday is a short evening. Girls' Night Out runs 5 to 8 p.m. across participating Old Town businesses. Saturday holds the rest. Here is the order in which it unfolds, according to Discover Old Town Greenwood's 2026 event listing:
- Noon to 6 p.m. The Mistletoe Handmade Market sets up along Madison Avenue.
- 1 to 4 p.m. Pictures with Santa at Faraday Toys.
- 2 to 4 p.m. Pictures with the Grinch at Bayberry Spa, courtesy of Modern Woodmen.
- 5:30 p.m. The lighted parade runs along Madison Avenue.
- 6:30 p.m. Tree lighting at Greenwood City Center.
- 7 p.m. The Greenwood Parks and Recreation drone show, best seen from Old City Park by the Greenwood Public Library.
The Santa and Grinch windows overlap, so families who want both photos can fit them into the same Saturday afternoon. The market closes at 6, a half hour after the parade steps off. Anyone shopping the vendor tables will want to finish before claiming a curb spot on Madison.
Last year the city paired the drone show with synchronized music through the Pyrocast app, so you could hear the soundtrack from anywhere you watched. Check the city's events page closer to the date for whether the app returns this year.
Spend Parade Day at the Places That Opened This Year
The open house exists to send people through local doors. Three of the doors on Old Town's Main and Madison have opened or grown in 2026.
Faraday Toys, 350 S. Madison Ave. Co-owners Aaron and Matthew Wardwell expanded the store in January into the former Dollar General space. The Daily Journal reported they also planned more community events. This year's Santa photos happen in that larger store. Matthew Wardwell described the open house to the Daily Journal last year as a way "to kick off the Christmas season without having to break the bank."
Melao! Cuban Cafe, 211 W. Main St. Owners Oscar and Sandra Canizares opened in mid-May, with regular hours starting May 18, according to the Daily Journal. This is the cafe's first holiday open house, and it sits a short walk from the Madison Avenue parade route.
Retro Paradise, 308 W. Main St. Gary Medley's shop for vintage media, games and collectibles held its grand opening in late May, the Daily Journal reported. It is a gift stop that turns up very different finds than the handmade market tables on Madison.
The Drone Show Crowd Will Be Standing Next to a Construction Site
The viewing spot for the 7 p.m. drone show is Old City Park by the library. Across Surina Way, behind that same library, Greenwood is building Veterans Memorial Park. It is half of a combined $7.5 million project with the new Fieldhouse Plaza. The Daily Journal reported in July that the city's Redevelopment Commission approved both.
The plaza plans read like a list of everything the holiday weekend currently borrows from streets and private lawns. They call for an event lawn, a pavilion, a game court, screens, a splash pad, a fire pit and a seasonal ice rink, with SCS Construction Services as the builder. Veterans Memorial Park, led by Paul St. Pierre, plans paths, flagpoles, benches, an eagle centerpiece and memorials linked to individual veterans through QR codes.
By September the plaza was "currently under construction near downtown Greenwood," the Daily Journal reported. The parks board had just approved its centerpiece, a Trekfit "Canyon Boulder" climbing wall. It will cost close to $250,000 and stand 12 to 15 feet tall, terracotta in color, with soft artificial grass underneath. Taggart told the paper the placement was deliberate. "It's right on Surina on purpose so when you drive by, it has a dynamic effect as well," he said. That contract depends on approval of the city's 2027 budget.
The ice rink is the piece that matters most for future Decembers, and its timing is still open. Greenwood's proposed FY2027 parks budget includes $383,000 for "Fieldhouse Plaza Ice Rink Management Services" and $250,000 for plaza equipment. A Sept. 9 council meeting recap called the rink operations estimate preliminary and still under negotiation. The rink has money penciled in, but the city has not announced an opening date or a completion date for the plaza. Skating is not on this winter's calendar yet.
So the drone show audience this year will be looking up from a park that sits next to the next chapter of the event. The open house has grown by adding to whatever space downtown already had. The plaza would give it a purpose-built space.
December Moves to the City's Side of the Calendar
After the open house, the season shifts to Greenwood Parks and Recreation programming, with Breakfast with Santa on the same Surina Way as the plaza site. These dates come from the city's events page, which says tickets for the two ticketed events go on sale Nov. 1.
- KiD CiTY Christmas, Saturday, Dec. 5, 5 to 8 p.m. A train ride through the Amphitheater Lighted Trail for selfies with Santa, plus hot cocoa, a bounce house and a take-home craft. Admission is $10, or $20 with a Ruby the Reindeer stuffie. Children under 2 get in free.
- The Lighted Trail, from Sunday, Dec. 6. A walk through Amphitheater Park with lights on from dusk until dawn. The city counts 85 trees of lights, 18 standing figures, a 12-arch candy cane tunnel and 3,600 lights on the bridge, totaling 42,840 lights. There will also be occasional entertainment from the stage during the month.
- Green Friday, Friday, Dec. 11. One day of 20% off annual memberships for KiD CiTY, The GYM, Freedom Springs, the dog parks and the Greenwood Fieldhouse. That same day only, non-residents can buy a Freedom Springs season pass, without the discount.
- Breakfast with Santa, Saturday, Dec. 12. Two seatings, at 8:30 and 10:30 a.m., at the Greenwood Community Center, 100 Surina Way. Tables are $50 for up to six people, with breakfast from SmokeHouse Catering, donut decorating and a photo with Santa.
The Lighted Trail's opening night is the day after KiD CiTY Christmas. Families who go to the ticketed train ride on Dec. 5 can come back and walk the same trail on foot any night through the month. Green Friday also falls before the plaza opens. A Fieldhouse membership bought that day covers the building the new plaza is named for.
If your holiday plans this year include hosting family who are thinking about a move to Greenwood, or you are weighing your own next move before the plaza and rink take shape, Home Strategy Group can walk you through what is changing around Old Town and Surina Way. Request your personalized market consultation, and we will start with the blocks you already know.
