Old Town Greenwood's Holiday Kickoff Weekend, From Girls' Night Out to the Drone Show Over Old City Park
October 29, 2026
October 29, 2026
At 7 p.m. on Saturday, Nov. 21, the organizer's schedule has Greenwood Parks & Recreation sending a lighted drone show over Old Town, with viewing from Old City Park beside the Greenwood Public Library. The parade will have just finished on Madison Avenue. The tree will have been lit half an hour earlier. If you turn around and look across Surina Way, you'll see a construction site where the city is building the space meant to host winters like this one all season long.
Greenwood's holiday season already has a home base on a short stretch of Madison Avenue and the parks around it. In the past year the city has spent its effort and money on making that same stretch work after dark and in the cold. The Holiday Open House weekend is the best chance this year to see what the stretch can already do.
Discover Old Town Greenwood bills the Greenwood Holiday Open House as the kickoff to the 2026 holiday season. It runs from 10 a.m. Friday, Nov. 20, through 7:30 p.m. Saturday, Nov. 21. Friday's main event is Girls' Night Out, 5 to 8 p.m., when the small businesses along Madison stay open late to "shop, sip and create."
The Festival Country Indiana listing adds a punch card. You collect stamps as you shop at participating businesses, and a full card earns a chance at prizes. If you pick up your card Friday night, Saturday afternoon can go to the market and the kids instead of a lap of every storefront.
On Saturday the whole weekend moves outdoors, and the times are tight enough to plan around. Here's the organizer's schedule:
| Time | What's happening | Where |
|---|---|---|
| 12 to 6 p.m. | Mistletoe Handmade Market | Along Madison Ave. |
| 1 to 4 p.m. | Pictures with Santa | Faraday Toys |
| 2 to 4 p.m. | Pictures with the Grinch, courtesy of Modern Woodmen | Bayberry Spa |
| 5:30 p.m. | Lighted Parade | Along Madison Ave. |
| 6:30 p.m. | Tree Lighting | Greenwood City Center, per the organizer |
| 7 p.m. | Greenwood Parks & Recreation Lighted Drone Show | Viewing from Old City Park by the Greenwood Public Library |
Santa and the Grinch overlap from 2 to 4 p.m., which helps if your family wants both photos. Faraday Toys and Bayberry Spa are separate stops, so give yourself time between them.
The two listings disagree on where the tree lighting happens. Discover Old Town Greenwood lists Greenwood City Center, and Festival Country Indiana lists Folktale Greenwood. Discover Old Town Greenwood runs the event, so check its page the week of the open house before you pick a spot.
The organizer's page still has sign-up forms for market vendors and parade entries. If your business, scout troop or club has wanted a float on Madison, the forms were open as of late October.
This is the first holiday open house since Greenwood's designated outdoor refreshment area, or DORA, opened to the public. The Daily Journal reported that the inaugural Old Town Greenwood Beer & Wine Fest, presented by Vino Villa with SmockTown Brewery, was the first event to use it on Oct. 17.
The district's map matches the holiday route closely. According to the Daily Journal, it runs along Madison Avenue from Fry Road south to Smith Valley Road, widens near Main Street to take in Market Plaza, and reaches east to Washington Street south of Main, including Old City Park and Craig Park. That covers the parade route and the drone show viewing area.
The businesses that had submitted completed applications by early October included Vino Villa, Planetary Brewing Co., Draft Day Pub, SmockTown Brewery and C&C Lounge. Drinks have to go in special cups with a DORA sticker and a QR code, and red signs mark where the district starts and ends. Temporary event vendors can apply for temporary permits. Neither holiday listing mentions the DORA, so whether drinks are part of Saturday's market depends on the permits granted for that day. This is general information, not legal advice. The city's DORA rules and the businesses' own signs decide where a cup can go.
Greenwood is the second Johnson County community with a DORA, after Bargersville approved one in 2024. Old Town's busiest holiday evening now takes place inside the district.
After the open house, the season moves from the merchants' calendar to Greenwood Parks & Recreation's events lineup. Much of it centers on Amphitheater Park.
The KiD CiTY train ride on Dec. 5 runs through the Lighted Trail a day before the trail's listed nightly start. That makes the ticketed event the earliest chance to see the lights.
The construction site across Surina Way explains why the open house weekend feels like a preview. In July, the Greenwood Redevelopment Commission approved the $7.5 million Fieldhouse Plaza. It will sit against the Greenwood Fieldhouse between Madison and South Meridian streets. The plans include an event lawn, an open-air pavilion, lounge seating, a game court, large video screens, a splash pad, a fire pit and an ice skating rink for the winter months. SCS Construction Services, the local contractor that built the Greenwood Sports Park, is doing the work. The RDC approved $6 million, and the other $1.5 million came from the state's READI 2.0 program.
The fieldhouse was designed with this plaza in mind. "When we built the fieldhouse, we actually built accordion doors so it could be integrated with this outdoor space and whatever future development we get just west of it," capital projects manager Kevin Steinmetz told the Daily Journal.
The project also takes in the long-planned Veterans Memorial Park, across Surina Way behind the Greenwood Public Library. That puts it next to the drone show crowd's viewing area. Rundell Ernstberger Associates' plan calls for walking paths, flagpoles, about 12 benches and a 16-foot centerpiece topped with an eagle. QR codes will link to "living memorials" about local veterans.
In late August, the parks board approved a climbing wall for the plaza: a Trekfit Canyon Boulder, about 12 to 15 feet tall, with 1,400 square feet of climbing surface for up to 12 people at a time. It costs close to $250,000, and approval depends on the 2027 budget. Parks director Rob Taggart told the Daily Journal that its spot was chosen deliberately: "It's right on Surina on purpose so when you drive by, it has a dynamic effect as well." The parks board also approved a 12-by-6-foot electronic screen for the back wall of the Greenwood Amphitheater, a $60,876 contract that includes electrical and structural work.
The rink is funded, but it has no opening date. In 2027 budget hearings, the city's finance team called Fieldhouse Plaza "a large cost driver" for 2027. Construction runs through tax increment financing and READI grants, while loose equipment such as benches, tables, the big screen and some of the ice rink gear comes from the parks budget, much of it from the Food and Beverage Tax Fund, according to the Daily Journal. No first skating season has been announced. This November, the plaza is a construction site you'll walk past on the way to the parade.
So the Nov. 21 parade, tree lighting and drone show all fit within a few blocks of Madison Avenue and Old City Park. A winter rink is already funded for the plaza across Surina Way.
If you're hosting family for the open house, or thinking about how a home near Old Town fits your own holiday routine, Shelly Walters and our team would love to talk about Greenwood with you, on Madison Avenue or over coffee. Let our family help your family. Contact us today.
Stay up to date on the latest real estate trends.
Partnering with our team means more than just buying or selling a home — it means having trusted experts by your side every step of the way. We combine deep market knowledge, innovative strategies, and a commitment to exceptional service to deliver results you can count on. Whether you’re a first-time buyer, a seasoned investor, or ready to sell your property, we’ll guide you with professionalism, integrity, and care.