Walk the Lebanon square on a Tuesday evening in September and you'll find volunteers taping up bunting for the Merchant Fall Reveal, the same folding tables that host Halloween on the Square in October, the same four restaurants that have anchored the block for years. Drive ten minutes west on Lebanon Road and you'll pass a construction fence around a 16.5-acre lot where a hotel is already going up. Those two scenes are not a coincidence. They're two different growth strategies running in the same town at the same time, and if you only pay attention to one of them, you're missing half of what's actually changing here.
The square is not getting bigger. It's getting busier, on a schedule. The new construction, the drive-thru lines, the retail square footage, all of that is landing somewhere else. Understanding which is which tells you more about how Lebanon actually works than any single headline about a new restaurant opening.
The Square Is Growing Its Calendar, Not Its Footprint
The dining cluster around the Wilson County courthouse has been stable for a while now. Town Square Social at 145 Public Square and Cedar City Brewing at 112 Public Square sit on opposite sides of the courthouse, less than a minute apart on foot. Angelo's Italian Restaurant on West Main and Sammy B's, one of the longest-running restaurants in town, round out a cluster that fits inside a 0.3-mile walk. None of that lineup is new. What's new is what happens on top of it.
Downtown Lebanon's merchant calendar adds two fresh fixtures to the fall this year: the Merchant Fall Reveal on September 12 and Halloween on the Square on October 25. Both slot in alongside a calendar that already includes a Shop Small and Tax Free Weekend and a Merchant Christmas Reveal in November. Earlier this year, Rock the Block brought free concerts to the square for four straight Friday evenings in May and June, food trucks starting at 5 p.m., local acts like the Nashville-based singer-songwriter Kendra and cover band Double Take playing to crowds who brought their own lawn chairs. Every food truck slot for this year's run filled before the season even started, according to Historic Lebanon Main Street, the nonprofit that organizes it.
That's the pattern. The square isn't adding square footage. It's adding dates to the calendar and trusting people to show up, and by the vendor waitlists, they are.
The New Construction Isn't Happening Downtown
Two of the biggest food and retail stories in Lebanon over the past eighteen months didn't happen anywhere near the courthouse.
Aubrey's opened at 1648 West Main Street in April 2025, a 7,636-square-foot building with a 1,700-square-foot patio and a full bar, the first new-construction sit-down restaurant Lebanon had seen since 2012. That's a 13-year gap between ground-up restaurant builds in a town whose square has four established restaurants and hasn't needed a fifth.
Then, in December 2025, In-N-Out opened its first Tennessee location at 915 South Hartman Drive, becoming the chain's tenth state. The Lebanon store, officially Store 429, runs a single drive-thru lane and had to buy extra adjacent property just to hold overflow traffic. It seats 74 indoors and about 30 more on a covered patio, employs roughly 75 people, and starts wages at $17.50 an hour. Mayor Rick Bell framed the opening as more than a restaurant landing, calling it a sign of a national brand investing directly in the community.
Both of those additions sit on corridors built for cars, not the walkable square. That's not an accident. It's where the land and the traffic counts are.
Five Oaks Is Building the Square's Job on the West Side
The clearest evidence of where Lebanon's growth dollars are actually going sits at the corner of Five Oaks Boulevard and Lebanon Road, where the Lebanon Planning Commission approved a mixed-use project called the Plaza at Five Oaks in April 2025. The anchor is the Shoppes at Five Oaks, more than 55,000 square feet of retail and restaurant space split across nine buildings and 22 individual spaces, with up to 5,700 square feet set aside for full sit-down restaurants. A three-story, 40,000-square-foot Cobblestone hotel with 50 to 60 rooms makes up the first phase of construction, which was already underway when WKRN reported on the project last year. Developers put the total project cost above $100 million.
What makes Five Oaks worth watching isn't the square footage. It's the reasoning behind it. Managing partner Russell Riebeling, a Lebanon native, has said the west side of town added plenty of new rooftops over the past several years without a matching increase in retail, food, or beverage options nearby. The plan calls for a central green space built specifically to host farmers markets, concerts, and seasonal festivals, the same kind of programming that currently only exists downtown. Future phases are slated to add a daycare, a fitness center, and a medical office building.
In other words, the west side is getting a working copy of what the square already does for downtown, built from scratch instead of inherited from a historic district that's been on the National Register of Historic Places since 1999.
The Fairgrounds Circuit Doesn't Pick a Side
There's a third gathering point in Lebanon that neither the square nor Five Oaks can claim, and it's been running longer than either debate about where new construction belongs: the fairgrounds circuit centered on the James E. Ward Agricultural Center and the Baddour Parkway event grounds.
The fall calendar out there is dense. The 21st Annual Fall Redneck Rumble takes over 945 East Baddour Parkway starting September 18. The Wilson County Senior Expo runs at the Farm Bureau Exposition Center on September 22. The 9th Annual IPRA Pro Rodeo saddles up at the Ag Center on October 2, and Foodieland returns to the same grounds later in the month. None of these events depend on a new building or a new lease. They depend on the fairgrounds being the fairgrounds, year after year, which is exactly why a 21st annual event and a 9th annual event can both exist without either one needing a ribbon cutting.
Meanwhile, the Chamber's own Taste of Wilson County lands on October 22 this year (rain date October 27), on the west lawn of the Wilson Bank & Trust main office on West Main Street, a location that splits the difference between downtown and the corridor growth happening further out. Attendance has averaged around 1,200 people a year, according to the Chamber, pulling from every direction of the county for one evening of food trucks and local vendors.
What This Actually Means If You Live Here
None of this is really a competition between the square and the west side. It's a division of labor. The square keeps its historic buildings and adds recurring civic dates instead of new leases. The corridors along West Main and South Hartman get the construction, the drive-thrus, the anchor restaurants that need parking lots. Five Oaks is trying to build both functions into one development from day one. And the fairgrounds keep doing what they've always done, pulling from all three at once.
If you've lived in Lebanon for a while, you've probably noticed pieces of this without connecting them. The In-N-Out line feels disconnected from the Merchant Fall Reveal until you realize they're both part of the same fall calendar, just aimed at different parts of town. The Plaza at Five Oaks isn't competing with the square. It's building a second one.
If you're watching how Wilson County keeps adding capacity without losing what makes downtown Lebanon feel like downtown Lebanon, that split is worth understanding, whether you're planning your weekend around a food truck lineup or thinking ahead to a move. ReLo Nash tracks this kind of local detail across Wilson County and the rest of greater Nashville because it's the difference between guessing at a neighborhood and actually knowing it. If you want a longer look at what's happening across Wilson County, our neighborhood guide is a good place to start, and if a move to this side of Nashville is somewhere on your calendar, book a relocation consultation with Misty Maynor and get a local read instead of a guess.
