"We want this to feel like the same neighborhood coffee shop, with a few new things to discover." Marnie Weber, co-owner of Anecdote Coffee, told the Daily Journal that line about 323 Market Plaza. Coffeehouse Five has run the shop there since July 2014, and it is set to pass to Anecdote in early December.
That handoff happens on the second of Old Town Greenwood's two big holiday Saturdays this year. The first Saturday, Nov. 21, belongs to the Madison Avenue merchants. It moves from a toy store to a spa to the parade route and ends in the park by the library. The second, Dec. 5, moves to the city's Amphitheater a few blocks east. It is also the last day Coffeehouse Five pours coffee in the building where the company started. The season changes hands twice in two weeks.
Nov. 21 Is a Madison Avenue Day
Discover Old Town Greenwood is calling its Holiday Open House the start of the 2026 holiday season. It runs Friday, Nov. 20 and Saturday, Nov. 21. Friday has Girls' Night Out from 5 to 8 p.m. Saturday packs almost everything else into about seven hours, from noon to 7 p.m. Festival Country Indiana's listing gives the event's overall hours as 10 a.m. to 7:30 p.m.
Here is Saturday, Nov. 21, in order:
| Time | What | Where |
|---|---|---|
| Noon 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 | Old Town Greenwood |
| 7 p.m. | Greenwood Parks & Recreation Lighted Drone Show | Viewing from Old City Park by the Greenwood Public Library |
Most of the afternoon happens inside individual Old Town businesses. Santa is at Faraday Toys, 350 S. Madison Ave., a store that looks very different from a year ago. In January 2026 the Daily Journal reported that Faraday had expanded into the former Dollar General space and now fills the whole building. The same story said the owners planned to remodel the original Faraday space for community movies, tabletop and video games, classes and other events. So a Santa photo there is also a look at what one Madison Avenue storefront has done with more room.
The Grinch is a short walk up the street at Bayberry Spa, 1 N. Madison Ave. The two photo windows overlap from 2 to 4 p.m., so a family can do both between market stops before the parade lineup starts filling Madison.
The vendor and parade sign-up forms are both on the Discover Old Town Greenwood events page, which shows how much of the day comes from local entries rather than outside production.
Where the Night Ends, and the New Rule on Those Blocks
After the 5:30 p.m. parade on Madison, the schedule moves to the 6:30 tree lighting. At 7 it reaches Old City Park, where Greenwood Parks & Recreation has set the viewing area for its drone show beside the library.
This is Old Town's first holiday season since the city created a designated outdoor refreshment area, or DORA. The Greenwood City Council approved it in a split vote in November 2025, as the Daily Journal reported. The first event planned around it was the Old Town Greenwood Beer & Wine Fest on Oct. 17, presented by Vino Villa with SmockTown Brewery.
The boundary covers most of where Nov. 21 takes place. According to the Daily Journal's October preview, the area runs along Madison Avenue from Fry Road south to Smith Valley Road. Near Main Street it widens to take in Market Plaza. South of Main it reaches east to Washington Street and includes Old City Park and Craig Park. The same story reported that until permanent street signs go up, the DORA operates only on designated event dates, using temporary signage.
When the DORA is active, the rules as the Daily Journal described them are:
- Alcohol only in DORA cups, which carry a DORA sticker and a QR code
- No outside drinks
- No more than two drinks per person at a time
- Up to 16 ounces for beer or malt beverages, 12 ounces for wine, cider or hard seltzer, and 10 ounces for mixed drinks with no more than 2 ounces of liquor each
- Red signs mark where the area begins and ends
- Business stickers show participation: red means no alcohol allowed inside, blue means alcohol is allowed, and green means the business sells it
The businesses named as completed applicants in that October story were Vino Villa, Planetary Brewing Co., Draft Day Pub, SmockTown Brewery and C&C Lounge. This is a summary of local news coverage, offered as general information and not legal advice. The City of Greenwood sets and enforces the actual rules.
Two Weeks Later, the Calendar Moves to Washington Street
On Saturday, Dec. 5, the season moves to the Amphitheater at 300 S. Washington St., and the City of Greenwood takes over as host. KiD CiTY Christmas runs from 5 to 8 p.m. Admission is $10, or $20 with a Ruby the Reindeer plush, and children under 2 get in free. The evening includes hot cocoa, a bounce house, a holiday craft to take home, and a train ride through the Amphitheater Lighted Trail for selfies with Santa. The city's page says tickets went on sale Nov. 1.
That train ride means KiD CiTY families see the Lighted Trail one night before it opens to everyone. According to the city, the trail opens Dec. 6, stays lit from dusk until dawn, and will have ambient entertainment from the stage at points during the month. The full build-out:
- 85 trees of lights
- 18 standing figures
- Five arches
- A 12-arch candy-cane tunnel
- Two seven-foot candy canes
- 3,600 bridge lights
- 10 light poles
That adds up to 42,840 lights, with Williams Comfort Air named as the sponsor. Indy's Child lists it as a free, self-guided holiday walk.
Nov. 21 is spread across Madison Avenue storefronts, the parade route and Old City Park. Dec. 5 and the weeks after it stay mostly in one park. The trail is also the only part of either weekend that stays up all month.
The Same Weekend at 323 Market Plaza
While the Amphitheater gets ready for its first big night, a few blocks away Coffeehouse Five is scheduled for its last day in Greenwood. Here is how that weekend is planned, according to the joint announcement the Daily Journal reported on Oct. 27:
- Saturday, Dec. 5: Coffeehouse Five's last day at 323 Market Plaza
- Sunday, Dec. 6: The Lighted Trail opens, and the coffee shop sits between owners
- Monday, Dec. 7: Anecdote Coffee plans to open the space as its third shop
The Greenwood shop was Coffeehouse Five's first, opened in July 2014. The Franklin location followed in March 2020 and Bargersville in February 2023, and both stay open. The company says it is moving to two retail locations so it can spend more time on roasting, wholesale coffee for other businesses, and mentoring people who are opening their own shops. The free counseling services tied to the business will continue, funded by proceeds from Franklin and Bargersville.
"Mentorship has always been part of who we are," co-owner Brian Peters said in the release, as quoted by the Daily Journal.
The new owners are not strangers to the business. The Daily Journal reported that the two companies are "coffee-in-laws," because the son of Coffeehouse Five's owners is married to the daughter of Anecdote's owners. Anecdote started in Southport, opened in Beech Grove in September 2025, and Greenwood will be its third location. That explains Weber's line about keeping "the same neighborhood coffee shop." The space is staying with the same extended family, just a different branch of it.
Market Plaza is also inside the DORA boundary that widens around Main Street. So the block where the coffee shop changes hands is part of the same few streets that host both Saturdays, the parade route, and the area the city has now marked out for walking around during events. For a household in Old Town, all of it is within walking distance from Nov. 20 to the Lighted Trail's opening night.
Amanda Cottingham Johnson has worked in Johnson County real estate since 1999, and part of that work is knowing which Old Town blocks get the parade, the drone-show crowd and the new coffee shop. If you're thinking about a home within walking distance of Madison Avenue, or wondering how Old Town's growing event calendar shows up when a nearby house is priced, Amanda Cottingham is glad to go through it with you. Let's Connect.
