What goes on a Halloween float in a Route 66 town during the road's centennial year? The Carlinville Rotary Club has set "Halloween on Rt 66" as the theme for its 87th Annual Halloween Parade.
That theme is more than a costume prompt. This year almost every Halloween event downtown connects back to the road. The most popular ghost story in town is a Route 66 and Prohibition story. The tour that tells it starts in a speakeasy on the South Side Square. Merchant's Night and the parade take place on the same Square that the Chamber already describes as part of "Historic Route 66" for Super Summer Weekend in July. If you live here, Halloween week this year is a week of costumes on the town's own history.
The Ghost Story Is a Road Story
The Haunted Carlinville tour, run by American Hauntings, frames Carlinville as a former "wide-open" mining town. The stories cover the corruption behind the Million Dollar Courthouse and the Prohibition bootleggers and rum-runners who used local roads to haul liquor to Chicago, traffic that brought Al Capone to town. The Chamber added the tour to its calendar for Saturday, Oct. 24, from 7 to 8 p.m.
Tickets were $25 per person, and every tour left from Route 66 Old Fashioned Speakeasy at 366 South Side Square, which is running seasonal drink specials. The whole 2026 season is sold out, and the operator's page says Haunted Carlinville returns in 2027. So if you didn't book early, you missed it this year. A tour that sold out at $25 a head in a town this size tells you the courthouse-and-bootlegger story still draws a crowd.
The speakeasy is still open to anyone the rest of the week, tour ticket or not, and it sits right on the Square where the next two big nights happen.
The Week at a Glance
| Date | Event | Time | Where |
|---|---|---|---|
| Sat., Oct. 24 | Haunted Carlinville Walking Tour | 7–8 p.m. | Departs 366 South Side Square, sold out |
| Thu., Oct. 29 | Merchant's Night on the Square | 5–7 p.m. | Downtown Square |
| Thu., Oct. 29 | Carlinville Area Hospital + Clinics Haunted Halloween Drive Thru | 5:30–7:30 p.m. | Venue not on the 2026 listing |
| Fri., Oct. 30 | Trick-or-treat hours | 5–8 p.m. | Citywide |
| Sat., Oct. 31 | MCDD Beaver Dam Dash | 10 a.m.–noon | Beaver Dam State Park, Shipman |
| Sat., Oct. 31 | Trick-or-treat hours | 5–8 p.m. | Citywide |
| Sat., Oct. 31 | 87th Annual Rotary Halloween Parade | 6:15 p.m. per the Chamber | Downtown Square |
The schedule fits into two crowded evenings. Thursday has two events on top of each other. Saturday runs from a morning trail race to a parade that starts inside the trick-or-treat window.
Thursday Has Two Events and Only Two Hours
Merchant's Night on the Square runs from 5 to 7 p.m. on Thursday, Oct. 29. The Chamber's annual events page describes it as a last-Thursday-of-October tradition. Streets around the Square close to traffic, and local businesses host safe trick-or-treating for children in costume.
That same evening, from 5:30 to 7:30 p.m., Carlinville Area Hospital + Clinics holds its Haunted Halloween Drive Thru. The Chamber's annual events page says the drive-through has taken place at the Macoupin County Fairgrounds, with haunted scenes, costumed characters, lights and candy, all put together by hospital staff and volunteers. The 2026 calendar entry still just says "save the date" and doesn't give a venue, so watch for the hospital's announcement before you drive out.
The two events overlap for an hour and a half, from 5:30 to 7. Families who want both have a few options:
- Start on the Square at 5 p.m., when Merchant's Night opens, and walk the closed streets first.
- Head to the drive-through once its location is confirmed, before it closes at 7:30.
- Go the other way around if the kids would rather finish with candy from the merchants than with a haunted drive.
This year the hospital has a bigger profile around town than usual. At a Sept. 29 event in Carlinville, it announced that the Macoupin Family Practice Centers in Carlinville, Gillespie and Mt. Olive had joined its organization, as the Enquirer-Democrat reported. The drive-through is still staff-built and volunteer-run, the same as in past years.
Saturday Runs From a Trail Race to the Parade
Halloween falls on a Saturday this year, so the day starts early and outside town.
The MCDD Beaver Dam Dash runs at Beaver Dam State Park in Shipman, with a 5K, a 10K and a one-mile Fun Run/Walk. The Chamber calendar lists it from 10 a.m. to noon. On RunSignup, the 5K and 10K cost $30 each plus a $1.40 service fee, and the Fun Run/Walk costs $15 plus a $0.95 fee. The race raises money for the Macoupin Center for the Developmentally Disabled and its services for adults with developmental disabilities.
Trick-or-treat hours in town are 5 to 8 p.m. on both Oct. 30 and Oct. 31, according to Great Rivers & Routes. The parade starts in the middle of that window on Saturday. Friday is the night with nothing else on the calendar, so it's the easier one for a long walk through the neighborhood.
The Parade Listings Disagree, So Plan on the Chamber's Version
Two public listings describe the 87th Annual Rotary Halloween Parade differently. The Chamber's listing is the one connected to the organizer and its registration form, and it says:
- Start time: 6:15 p.m., with the listing running to 8 p.m.
- Theme: Halloween on Rt 66
- Entries: Pre-registration is required to be in the parade, through the form linked from the Chamber page.
The Great Rivers & Routes tourism listing gives a 6 p.m. start, running to 7:30 p.m., and says no pre-registration is required. It also gives the route. The parade starts at the Carlinville Plaza and runs down North Broadway, which is IL Route 4, to North Broad and the Square. Floats and vehicles line up at the Plaza by 5 p.m. for judging, and costumed walkers meet for judging in the City Hall parking lot at 5 p.m., joining the parade from there.
If you're building a float, register through the Chamber form and keep the 5 p.m. lineup times in mind. If you're watching from the curb, getting to the Square by 6 p.m. covers both start times. Check with the Chamber that week if the route matters for where you park or set up chairs.
Floats roll down Route 4 and finish on the Square, where Super Summer Weekend happens each July "along Historic Route 66." A Route 66 Halloween float will spend the parade on the road it's dressed up as.
What Comes After the Costumes
Halloween is the third Route 66-flavored weekend downtown this fall. Brave Days, which the Chamber describes as a makers-and-merchants festival with "Route 66 spirit," filled the Square on Oct. 9 and 10. The Enquirer-Democrat reported that 55 vendors came for the two days.
Then the calendar slows down:
- Market Days, Saturday, Nov. 7, 9 a.m. to 3 p.m. This is the last one of the year. The series runs the first Saturday of each month from April through November.
- Christmas in Carlinville, Dec. 4–6. The event takes place at several venues, including the downtown Square, the courthouse, the Historical Society, the Elks Lodge, Country Gypsy, The Well on Main and the Macoupin County Fairgrounds.
- Carlinville Christmas Market, new location. The market has moved from Cross Church to the Macoupin County Fairgrounds at 21368 State Route 4.
If you missed the ghost tour this year, the 2027 dates are the ones to watch. The Million Dollar Courthouse, the bootlegger roads and the speakeasy on the South Side Square aren't going anywhere.
A lot of what makes a Route 66 town feel like itself is the building stock along the road and around the Square: storefronts, older homes, and the lots and acreage on the edges of town. If you own a piece of that in or near Carlinville and want to know what it's worth in today's market, Land & Home Real Estate works out of our original office just off the Square, and we're glad to walk it with you. Request a Property Valuation whenever you're ready.
