On the evening of September 24, someone stood on the courthouse lawn and talked about Truman Capote for a while, and then the crowd went home. That event is already behind Monroeville now. What comes next is the part worth watching: three more named events, three more weekends, all staged on the same three blocks around the old courthouse. TailChaser lands on October 10. The Witches Ride and Ghouls Night Out follows on October 15, with witches registering for $15 a head to ride down Main Street at 6:30 in the evening while everyone else watches for free. The Halloween Bash closes it out on October 31.
Four different events, four different formats, one stretch of sidewalk. A costume-and-community day. A nighttime parade with a registration fee. A legacy celebration for a hometown writer. A full holiday street festival. None of that would have been possible on this square a decade ago, and the reason has less to do with enthusiasm and more to do with what's actually standing on those blocks now.
The Square That Couldn't Have Done This in 2014
Before Monroeville Main Street existed, downtown had a 31 percent vacancy rate. That number comes straight from the organization's own account of where things stood, and it lines up with a familiar story for small Alabama towns that lost a manufacturing base: the textile industry that once supported the district thinned out, and the storefronts around the courthouse square emptied out with it. A quarter to a third of the ground floor space downtown sat unused.
Main Street Monroeville formed in 2014 to change that, and the town spent a decade doing something less glamorous than a ribbon cutting: coordinating grants, courting building owners, subdividing oversized commercial spaces, adding upper-story housing where there used to be storage. By 2024, that decade of unglamorous work earned Monroeville the Great American Main Street Award, sponsored by The Hartford. Monroeville was one of three national winners that year, and the first Alabama community to win it at all.
The dollar figure attached to that recognition is $10.9 million in public and private reinvestment since the organization's founding. Since 2014, that money has gone toward renovating 42 properties, adding 15 new loft apartments, and creating 23 affordable storefronts. For a town with a population just under 6,000, that is not a rounding error. It is the difference between a square that could host one struggling festival a year and a square that can carry four structurally different events across seven weeks without running out of foot traffic or open storefronts to spill into.
The Backdrop That Never Has to Be Built
Part of what makes back-to-back events possible without visible strain is that a layer of the square's identity is permanent. In 2019, Monroeville unveiled the Literary Capital Sculpture Trail: 14 bronze sculptures spread through the historic district, honoring the ten writers credited with making Monroe County the literary capital of Alabama, including Harper Lee, Truman Capote, journalist Cynthia Tucker, and novelist Mark Childress. The pieces were created by University of Alabama sculpture students under Professor Craig Wedderspoon, and the project was sponsored jointly by the City of Monroeville and JWJ Investment Properties.
At the unveiling, Mayor Sandy Smith described the trail as something that would inform, entertain, and educate while adding to the district's quality, and Anne Marie Bryan, Main Street's executive director, called it the fulfillment of a goal the organization had held since 2015. Those sculptures are still standing on the same lawns and sidewalks where TailChaser, the Witches Ride, and the Halloween Bash will each set up. So are the Johnna Bush murals scattered through downtown. None of that art needs to be trucked in, assembled, or struck down after the crowd leaves. It is simply there, which means every event that uses the square inherits a backdrop that a temporary festival budget could never afford to build from scratch.
People Actually Sleep Above These Storefronts Now
The other piece of the mechanism is upstairs. A decade ago, the buildings ringing the square were mostly empty on the ground floor and unused above it. That has changed on a couple of specific addresses worth naming.
The Faulk Building at 32 North Alabama Avenue sat as a vacant historic structure until developer Billy Jones renovated it, drawing on a $5 million New Markets Tax Credit loan pool that helped restore nine historic buildings downtown. Jones won the 2022 Excellence in Historic Preservation Award from Main Street Alabama for that work, and the building now holds four fully furnished lofts available for short-term rental. A few blocks over, JWJ Investment Properties took an abandoned 1940s-era county maintenance shop and turned it into the Shop & Loft at 66, pairing a renovated commercial front with actual living space behind it.
Neither project was built for festival season. Both were built because a building that used to sit empty now has someone sleeping in it, whether that's a resident in one of Main Street's 15 new loft apartments or a visitor renting a night in the Faulk Building. That matters for a square trying to run four events in seven weeks, because it means the district has activity and eyes on it between events, not just during them. A square that only comes alive one Saturday a year has to rebuild momentum from zero every time. A square with people living above the storefronts starts every event weekend with a baseline of life already in place.
What's Actually on the Calendar
For anyone trying to plan around it, here's what's confirmed for the rest of the run:
- October 10 — TailChaser, downtown on the square
- October 15 — Witches Ride and Ghouls Night Out, 6:30 p.m., departing Main Street through the downtown streets. Riding costs $15 to register; watching is free. Registration forms are available at City Hall, and questions go to Special Events Director Dawn Brewton at 251-923-7470.
- October 31 — Halloween Bash, downtown
Each of these pulls a different crowd for a different reason. TailChaser reads as a daytime, family-facing event. The Witches Ride is built around spectacle after dark, with a modest fee that funds the ride itself rather than general admission. The Halloween Bash closes the month the way most small-town Halloweens do, as a full street event rather than a single parade moment. Three different shapes, same three blocks, same bronze plaques and painted walls in the background of all three.
Why the Shape of This Matters More Than the Count
It would be easy to read this as just a busy calendar. The more useful read is that Monroeville's square has been engineered, deliberately and over a decade, to carry weight it couldn't have carried in 2014. A 31 percent vacancy rate does not host three format-different events in one month. A district with 23 new affordable storefronts, 15 new loft apartments, and $10.9 million in combined investment does, because the fixed costs of hosting anything downtown, filled storefronts, people living upstairs, permanent public art that doesn't need setup, have already been paid for by a decade of Main Street work rather than by whichever committee is running this particular Saturday.
That's a different kind of civic infrastructure than a parks budget or a festival grant. It's the reason a town under 6,000 people can run a costume day, a nighttime parade, and a full street festival within three weeks of each other and have each one look like the square was built for exactly that event, rather than borrowed for it.
I keep a close eye on what's actually happening on the ground in the towns I work, not because it changes what a house is worth on paper, but because it's the kind of detail that tells you whether a downtown is coasting on nostalgia or genuinely being rebuilt. Monroeville's square falls firmly in the second category right now. If you're curious what that kind of investment looks like from the inside, whether you already call Monroeville home or you're weighing whether it should be, Kelley Real Estate Co is a good place to start that conversation. Get a Free Home Valuation whenever you're ready to see where your own piece of it stands.
