Greenwood's Holiday Season Starts Twice, and Old Town Goes First

Greenwood has two holiday seasons, and each has its own organizer, location and schedule. Discover Old Town Greenwood starts its season on Madison Avenue on Nov. 20 and 21, the weekend before Thanksgiving. Greenwood Parks & Recreation starts its season two weeks later, on Dec. 5, at the Amphitheater. The two don't overlap. Planning around only one of them means missing half of what the city puts on in November and December.

Old Town's kickoff arrives before many households have started thinking about the holidays. The Amphitheater's runs for weeks.

Old Town's season fits into one weekend

Discover Old Town Greenwood calls its Holiday Open House the start of its 2026 holiday season. It begins Friday, Nov. 20, with Girls' Night Out from 5 to 8 p.m. Most of the event happens the next day.

Here is the organizer's Saturday, Nov. 21 schedule, in order:

1. Noon to 6 p.m. The Mistletoe Handmade Market runs along Madison Avenue.
2. 1 to 4 p.m. Pictures with Santa at Faraday Toys, 350 S. Madison Ave.
3. 2 to 4 p.m. Pictures with the Grinch at Bayberry Spa, 1 N. Madison Ave., courtesy of Modern Woodmen.
4. 5:30 p.m. The lighted parade along Madison Avenue.
5. 6:30 p.m. The tree lighting at Greenwood City Center, 300 S. Madison Ave., per Discover Old Town Greenwood.
6. 7 p.m. The Greenwood Parks & Recreation lighted drone show, with viewing from Old City Park by the Greenwood Public Library.

The list shows how much happens in a short span. Santa and the Grinch overlap from 2 to 4 p.m. at shops at opposite ends of the Madison Avenue blocks, Faraday Toys on the south end and Bayberry Spa just north of Main Street. After that, the parade, tree lighting and drone show come one after another in 90 minutes. The two photo windows are the only part of the day that forces a choice. Everything from 5:30 on is a single walk south toward City Center and over to the park by the library.

Festival Country Indiana's listing adds one more detail. Shoppers can pick up a punch card, collect stamps at participating businesses and earn a chance at prizes. That makes the Friday and Saturday shopping hours part of the event, along with the evening program.

Some stops are newer than the event itself. Retro Paradise, a vintage media, games and collectibles shop at 308 W. Main St., opened this past spring, the Daily Journal reported in May. This will be its first holiday season on the block. We have an earlier post on how Old Town has been rebuilding its Main Street corridor one owner-run business at a time, and the open house is that same group of shops putting on one shared event.

The city's drone show entry is waiting on its 2026 update

The City of Greenwood's events page has not been updated for this year's drone show yet. As of late October, the entry starts with this line:

STAY TUNED FOR ALL 2026 INFO!!!!!!!

The text below that line puts the drone show on Nov. 22, right after Old Town's lighted parade. Nov. 22 was the Saturday of last year's event. In 2026, Nov. 22 falls on a Sunday. Both Discover Old Town Greenwood's own page and the Festival Country listing put the 2026 open house on Friday, Nov. 20 and Saturday, Nov. 21.

Nov. 21 is the date to plan around. The organizer runs the event and posted the 2026 schedule, and the city page says itself that its 2026 details are still coming. The same city entry describes last year's show as 100 drones, with synchronized music through the Pyrocast app. The drone show is also not a new feature. The Daily Journal's preview of the 2025 open house called last year's show the first of its kind, so 2026 is its second year.

Then two quiet weeks, with Thanksgiving in the middle

After the drone show on Nov. 21, neither organizer has another public holiday event on its 2026 schedule until Dec. 5. Thanksgiving falls on Nov. 26, in the middle of that gap.

The gap gives households one useful thing to do. Tickets for the Parks Department's two ticketed December events, KiD CiTY Christmas and Breakfast with Santa, went on sale Nov. 1 through the city's registration system. Breakfast with Santa has two seatings, and KiD CiTY Christmas runs on one evening only. That makes the weeks around Thanksgiving the time to decide which December dates are worth booking.

The Amphitheater takes over Dec. 5 and stays lit through December

The Parks Department's season works differently from Old Town's. It is spread over several weeks, and its centerpiece, the Lighted Trail, is open every night on a self-guided schedule. The ticketed events come in the opening weekend and the one after.

KiD CiTY Christmas on Dec. 5 includes a train ride through the Amphitheater Lighted Trail for selfies with Santa, along with hot cocoa, a bounce house and a holiday craft to take home. The city lists the trail as opening to the public "beginning December 6." That puts KiD CiTY ticket holders on the trail the night before it opens to everyone else.

The trail itself is the longest-running part of the season. According to the city, it has 85 trees of lights, 18 standing figures, five arches, a 12-arch candy cane tunnel, two 7-foot candy canes, 3,600 lights on the bridge and 10 light poles. That adds up to 42,840 lights, on from dusk until dawn, with background entertainment from the stage at times during the month. Old Town's evening program happens on one Saturday. The trail is open every night from Dec. 6 on, for a walk after dinner or with visiting family.

Green Friday on Dec. 11 matters to anyone who uses the parks system year-round. For one day, the city takes 20% off annual memberships to KiD CiTY, The GYM, Freedom Springs, the dog parks and the Greenwood Fieldhouse. Non-residents can also buy a Freedom Springs season pass that day, though the discount doesn't apply to it. Families who used Freedom Springs over the summer, or followed the Amphitheater's fall concert series after the pool closed, can buy next year's passes in the middle of the holiday season.

Breakfast with Santa on Dec. 12 is catered by SmokeHouse Catering. The menu is two pancakes, two sausage links, scrambled eggs and cheesy hash brown casserole, followed by donut decorating and a photo with Santa. Children under 2 don't count toward the six seats at a table.

What isn't open yet

The Fieldhouse Plaza won't be part of this season. In July, the Daily Journal reported plans for a pavilion, an event lawn, a splash pad, a fire pit and a seasonal winter ice rink. In September, the paper reported that parks officials had approved an interactive climbing sculpture for the plaza and a 12-by-6-foot electronic screen for the Greenwood Amphitheater, with spending on the climbing feature dependent on the 2027 budget. The plaza was still under construction in September, and no opening date had been announced. For 2026, the season's two locations are still Madison Avenue on Nov. 20 and 21 and the Amphitheater from Dec. 5 on.

Add both dates to the calendar now. Nov. 21 covers Old Town's market, parade, tree lighting and drone show. Dec. 5 starts the Amphitheater's monthlong run. Tickets for the December events have been on sale since Nov. 1.

At Duke Collective, we track Greenwood's calendar the same way we track its market, week by week and block by block. If the holidays have you thinking about what your home on these streets is worth heading into 2027, get your free home valuation, or browse our Greenwood neighborhood guide between the parade and the lights.