On Saturday, December 2, 2023, the City of Webster Groves' calendar announced a "first ever Holiday Festival" in Old Orchard. Santa and Mrs. Claus sat in the gazebo from noon to 2 p.m., a Show Starters holiday performance ran from 4:30 to 5 p.m., and the schedule's last line read "Flip the switch! Tree lighting in Gazebo Park" at 5 p.m.
Three Decembers later the lighting is still the final event, but the day leading up to it is much longer. The city's 2026 listing calls the lighting ceremony "the finale for the holiday festival." Santa now arrives at 11 a.m., there is a petting zoo, a sweepstakes drawing, two youth performing groups, and the switch flips at 5:15 p.m. Anyone who used to show up just for the lighting will now be arriving at the end of a full day the Old Orchard business district has built around it.
How a business district ended up hosting the city's lighting
The festival has a paper trail at City Hall. The Old Orchard Special Business District Advisory Commission met at 8 a.m. at City Hall and on Zoom that summer. Its approved minutes from July 9, 2024 show members planning that December's festival five months in advance, proposing a subcommittee that would include district businesses, and assigning the city liaison to coordinate the lighting ceremony.
Five months later the second edition ran on Saturday, December 7, 2024, from 10 a.m. to 5 p.m., and FOX 2 covered it as a day of Santa, shopping, and the tree lighting. The 2025 edition, billed as the "3rd Annual" in the city's listing, fell on December 6. The city's Friday Page newsletter on December 5, 2025 promoted shopping, dining, performances, and a 5 p.m. Gazebo Park lighting for the following day.
Merchants, a city advisory commission, and the city share one Saturday, and the lighting is timed for dusk so that people arriving for the gazebo have already spent the day on Big Bend.
The Saturday, December 5 timeline
This is the city's published schedule for the 4th annual festival:
| Time | Where | What |
|---|---|---|
| 10 a.m. | Across the district | Shopping and dining open |
| 11 a.m. to 2 p.m. | Gazebo Park | Santa and Mrs. Claus |
| 12:30 to 3 p.m. | Gazebo Park | Cowboy Critters Petting Zoo |
| 3:30 p.m. | Gazebo Park | Find the Elf winners drawn, one child and one adult |
| 4:30 p.m. | Gazebo Park | Live music begins, with the Hixson Middle School choir and Gateway Center for Performing Arts |
| 5:15 p.m. | Gazebo Park | Gazebo Park lighting |
Gazebo Park is at 8180 Big Bend Boulevard. On the district's festival page, the day runs 10 a.m. to 5 p.m., which covers the shopping hours. The city's listing runs to 6 p.m. so the evening program fits. According to the district, every business "will be celebrating in its own special way," so the gazebo schedule is only part of what happens that day.
The festival covers more than one block. It starts at Summit Avenue on East Lockwood and runs east along Big Bend Boulevard to Dale Avenue, plus the adjoining stretch of South Old Orchard Avenue.
The scavenger hunt is the reason to start early
The festival's Find the Elf Sweepstakes starts Thanksgiving weekend, not on December 5. According to the city, you pick up an Elf Pamphlet, collect stamps at each stop, and work toward a holiday BINGO. The district's events page lists Gazebo Park as the hunt's home base. The drawing is at 3:30 p.m. on festival day, and the city's listing says plainly: "You must be present to win!"
The hunt fills the gap between Santa's last visit at 2 p.m. and the music at 4:30. Families who collect stamps after lunch end up at the gazebo for the drawing, then stay for the choir and the lighting. A second promotion runs alongside it. Old Orchard's $1,000 Shopping Spree is listed from November 9 through December 6, so it is already underway on the day this post is published.
Where the afternoon goes on Big Bend
The festival's success depends on the storefronts between Lockwood and Dale. These businesses are on the district's directory or took part in its 2026 events, and they are a practical way to plan the hours between the gazebo events:
- Big Sky Cafe, 47 South Old Orchard Avenue, on the side street the festival footprint includes.
- DD Mau, 8169 Big Bend Boulevard, described by the district as a fast-casual Vietnamese eatery.
- The Annex, 8122 Big Bend Boulevard, appears in the district's May route as "The Annex Coffee and Foods/Half Pint." St. Louis Magazine reported the opening of Half Pint, its ice cream and candy shop at 8124 Big Bend, in January 2024.
- Bijoux Chocolates, 7930 Big Bend Boulevard, Suite A. It served hot chocolate at the district's fall festival.
- Amy's Cake Pop Shop, 7967 Big Bend, a bakery and gift shop.
- Civil Alchemy at 8154 Big Bend, Forth and Home at 8137 Big Bend, and The Little toy shop at 8143 Big Bend, all within a few doors of Gazebo Park.
Frisco Barroom and Vanilla Sugar Bake Shop were listed with Big Sky Cafe, Bijoux, and The Annex as participants in the district's May event. Beignet All Day and Cyrano's Café were on the lineup for its October fall festival.
There are also two newer stops in the 7900 block. In its business notes, the Webster-Kirkwood Times reported Blackbird Yoga's grand opening at 7930 Big Bend, Suite C, in July 2026, and covered The Only Facial at 7961 Big Bend later that month. Blackbird Yoga shares the 7930 address with Bijoux Chocolates, so a single stop covers both.
December is the third event on Old Orchard's calendar
The Holiday Festival is the last of three seasonal events the district now holds each year. Old Orchard in Bloom took place on Saturday, May 9, 2026, with participating businesses open 10 a.m. to 5 p.m. The Fall Festival was October 24 and 25. DD Mau planned fall drinks and family activities for it, and Amy's Cake Pop Shop planned free samples.
All three use the same approach. Each event covers the whole district, and each business runs its own part of it. The district does the work of a downtown events office, and the city's annual Gazebo Park lighting is the December event's finale.
For planning purposes, the 4th annual festival works best as an afternoon, not a 5 p.m. visit. Pick up an Elf Pamphlet Thanksgiving weekend, collect stamps on Big Bend over the following week, get to Gazebo Park by 3:30 on December 5 for the drawing, and stay through the 4:30 music for the 5:15 p.m. lighting.
If you live near Old Orchard, the Holiday Festival is one of the clearest ways to see how this corner of Webster Groves works together. If you're thinking about a move nearby, or just want to talk through the area, Meggin Martin is happy to meet for a coffee on Big Bend. Let's connect.
