The Downtown Lebanon events page gives Halloween on the Square a single line: October 25. Below that, the Main Street calendar for the weeks before it lists eleven separate items between October 10 and October 24. They include a Fleetwood Mac tribute, a comedy night, a Beetlejuice movie event, a supper club, a songwriters' round, two pop-up art classes, a Halloween trivia night, a trunk-or-treat market and a ghost-story concert in a college chapel.
The square gets one afternoon. The rest of the season takes place inside a handful of downtown buildings, mostly after dark, and much of it is aimed at adults. Families who plan around those buildings get more out of the season than families who plan around the one Sunday.
The buildings hosting the season
Four venues carry most of the October calendar, and each one holds a different kind of night.
The Capitol Theatre at 110 West Main Street is a renovated historic theater that now runs as a multipurpose venue for theater, music, movies, and private and public events. This month it has a Beetlejuice movie event on Thursday, October 15, at 6:30 p.m. It also has Brainiac Halloween Trivia + Movie Night on Saturday, October 24, from 6 to 9 p.m. The calendar doesn't name the films, so the theater's own site is the place to check for details.
The Mill at Lebanon at 300 North Maple Street occupies the former Lebanon Woolen Mills, which began operating in 1908. The building is now a mixed-use development with offices, event spaces and creative studios. Its South Loft hosts the IPOP Creatives Writers' Lounge every fourth Thursday at 7 p.m. The lounge is an evening of live original music, with songwriters telling the stories behind their songs. This month's falls on Thursday, October 22, from 7 to 9 p.m.
Demeter's Common at 116 North College Street was profiled by Wilson County Source in 2023 as a grocery store that stocks local growers and makers and has a coffee bar and prepared food. Its October Supper Club is Saturday, October 17, from 7 to 9 p.m. The calendar listing doesn't include a menu.
Olivia Cocktail & Oyster Bar at 114 E. Main St. is a locally owned bar serving craft cocktails, curated wine, small and large plates, and raw or baked oysters. It closes out the month's evening calendar, covered in the age section below.
None of these venues was built for Halloween. They already run events, and in October their regular programming takes on a seasonal theme. That's why the season feels spread out: it follows the venues' schedules, and the square's single afternoon is only one of the dates.
Thursday, October 22, has two things going on
The busiest weeknight of the month is Thursday the 22nd, and its two events draw very different crowds.
From 5:30 to 8 p.m., the Lebanon Wilson County Chamber of Commerce holds its 17th annual Taste of Wilson County on the Wilson Bank & Trust West Lawn. The calendar listing gives the address as the Wilson Bank & Trust main office at 623 W. Main Street. The Chamber says the event has averaged about 1,200 attendees a year. The money raised supports the Wilson County Business & Education Coalition and Chamber education programs, including teacher grants, Wilson Books from Birth, Tennessee Scholars and student scholarships. If the weather is bad, the rain date is Tuesday, October 27.
At 7 p.m. that same night, the Writers' Lounge starts at The Mill. The Taste ends at 8, so the two overlap for an hour. Someone who wants both can eat on the West Lawn early and drive over to North Maple for the second half of the round.
The weekend of October 23 to 25 is the busiest stretch
The busiest three days of the season come right before Halloween on the Square. Here's how the Main Street calendar lays them out, along with the venue and age details each listing provides.
| Date | Event | Where | Time | Age note |
|---|---|---|---|---|
| Fri., Oct. 23 | Spooky Sips & Strokes pop-up class | Wild Colors Creative Design Studio | 6–8 p.m. | Not listed |
| Fri., Oct. 23 | Ghouls and Goblets with Sinister in Song | Cumberland University, 1 Cumberland Dr. | 7–10 p.m. | Concert all ages, rated PG-13; tour 21+ |
| Sat., Oct. 24 | Mommy + Me pop-up class | Wild Colors Creative Design Studio | Morning | Parent and child |
| Sat., Oct. 24 | Brainiac Halloween Trivia + Movie Night | Capitol Theatre | 6–9 p.m. | Not listed |
| Sat., Oct. 24 | Tattoo Cornucopia Trunk or Treat Halloween Market | Venue not listed | 6–10 p.m. | Not listed |
| Sun., Oct. 25 | Halloween on the Square | Lebanon Public Square | Time not yet posted | All ages in 2025 |
Friday's main event is the Cumberland University show. Cumberland University, Historic Lebanon Main Street and Stage Local present it together. Stage Local says the concert takes place inside the university's historic Baird Chapel and is followed by drinks, s'mores by a fire and a ghost tour across campus. The concert is open to all ages and rated PG-13, and the Ghouls and Goblets tour portion is 21+. In practice, a family could attend the concert together, and then the adults would have to decide whether to stay for the tour.
Saturday runs from morning to night. It starts with the Mommy + Me class at Wild Colors. In the evening, trivia at the Capitol Theatre and the Tattoo Cornucopia market run at the same time, starting at 6 p.m.
Sunday is the square's afternoon. As of today, the 2026 listing gives the date and the Public Square location but no start time. For a sense of what to expect, last year's Chamber listing ran from 2 to 4:30 p.m. on October 26, 2025. The City of Lebanon and the Lebanon Wilson County Chamber of Commerce presented it. The 2025 event featured food, photo spots, activities for all ages, a costume contest and candy booths hosted by local businesses. This year's details may be different, so check the Downtown Lebanon events page before setting a time.
Where the kids' events fall, and where the 21+ ones do
Lay the whole season out by age and a pattern shows up. The events clearly meant for children happen in daylight, and two of them are outside the downtown core. The adult events cluster in the evenings, and the latest ones are inside downtown bars.
Daytime and family events:
- Mommy + Me at Wild Colors, Saturday morning, October 24
- Halloween on the Square, Sunday, October 25, on the Public Square
- Halloween in the Grove, Saturday, October 31, from 2:30 to 4 p.m. at Fiddlers Grove Historic Village, 945 East Baddour Parkway, with trick-or-treat stations, games, free hot dogs, a costume contest and a ghoul parade
Evening and 21+ events:
- Ghouls and Goblets tour, Friday, October 23, after the Baird Chapel concert
- Sinister in Song at Olivia, Thursday and Friday, October 29 and 30, with seatings at 5 and 7 p.m. Stage Local bills these as "After Dark" shows. They're adults-only and 21+, with different vocalists and set lists each night, and food and drinks are sold separately.
The Olivia shows fall in the final days before Halloween, and Stage Local's calendar treats them as a separate run from the Cumberland concert. Together they make up the series Stage Local lists as October 23, 29 and 30, 2026. Seats at a two-seating show in a bar are limited, so these are the October events most worth booking early. Details are on Stage Local's Sinister in Song page.
For families, the 31st has a simple answer. Halloween in the Grove ends at 4 p.m. at Fiddlers Grove, well before neighborhood trick-or-treating usually starts. The free hot dogs cover an early dinner.
The same calendar runs into the holidays
Downtown events don't stop after Halloween. The Downtown Lebanon list goes on to the Merchant Christmas Reveal on November 7, Black Friday Power Hour on November 26, Small Business Saturday on November 28, the Christmas Parade on December 6 and Christmas on the Square on December 12. The October season follows the same pattern as the rest of the year. The square hosts a few named days, and the buildings around it keep up a steady stream of smaller events in between.
Shawn Wright has lived in Rutherford County his whole life and keeps up with what's happening across Middle Tennessee, including evenings like these in downtown Lebanon. If you're spending more time in Lebanon and want to know how its downtown and the areas around it are changing, CENTURY 21 Wright Realty is glad to talk it through. Let's Connect.
