Two storefronts changed on the WestSide in the past year, one pouring cocktails where a backyard cookout idea finally found a building, the other selling candles where a family known for cutting monuments decided to try something softer. Both sit in the same historic commercial district where the City of Cookeville is planning a five-acre public project on land it purchased nearby. The businesses are open now, and the city's construction timeline is still to come.
The Cookout That Took Thirteen Years to Become a Building
Chill Billy's Lounge held its grand opening at 102 N Cedar Avenue in October 2025, and the Cookeville-Putnam County Chamber of Commerce was there to mark it. The concept belongs to Toni and Bryon Mowrey, and its backstory runs longer than most new restaurants get to claim. The idea started in 2012 as informal cookouts among friends, grilling and hanging around long after the food ran out, and it stayed an idea through the years the Mowreys spent building Full Rack BBQ before they finally opened a room built specifically for it.
What they built is a craft cocktail and elevated bar food spot with an open kitchen, serving breakfast, lunch and dinner seven days a week. The Chamber's own description calls it "the newest spot for classic and craft cocktails, excellent food and good times in Cookeville's West Side." A city business license filed in September 2025 lists the entity as Chill Billy's LLC, doing business as Chill Billy's Lounge, at that same Cedar Avenue address.
The location matters as much as the concept. Cedar Avenue is one of the two streets the City of Cookeville named specifically when it explained why its own biggest WestSide project needed fixing in the first place.
A Few Doors Over, a Monument Company Tries Candles
Westside Luxuries opened at 149 W Spring Street, a few minutes' walk from Chill Billy's, with a grand opening covered by the Upper Cumberland Business Journal and photographed by Putnam County Mayor Randy Porter. The boutique was founded by lifelong Cookeville residents, the same family behind Harris Monuments, moving from a business built on stone and permanence into one built on fragrance and local art. The Chamber's language for the new shop calls each piece "thoughtfully curated to feel elevated, warm, and welcoming."
It is a small opening in square footage but a real one in what it signals. A family with an established name in one kind of Cookeville commerce chose the WestSide, not the mall corridor or a strip center off the interstate, for a completely different kind of business. That is not the behavior of people betting against the neighborhood.
The Five Acres the City Bought, Then Explained, Then Expanded
Both of those openings sit in the same historic WestSide district that surrounds the 39 Depot Master Plan, the city's name for roughly five acres it purchased at the southwest corner of Depot Street and South Cedar Avenue. The project's public timeline is worth laying out plainly, because it shows which pieces are open today and which are still ahead.
In September 2025, the City Council retained a design team, ASA Engineering & Consulting alongside the Chattanooga firm Tinker Ma, after interviewing four firms for the job. Cookeville Mayor Laurin Wheaton said at the time the goal was a plan that was "creative, strategic, functional, historically sensitive." The same announcement set a construction target: break ground on the parking lot component in the first quarter of 2026, and start road improvements before the end of the third quarter of 2026, including a long-discussed fix for the intersection locals call malfunction junction at Cedar and Broad.
By July 2026, the scope had grown well beyond a parking lot. The City Council approved a full master plan that includes:
- Space reserved for a potential farmers market
- A museum
- A stage and entertainment plaza
- A gazebo area
- Multiple green spaces
- Public restrooms
- A historical marker
- A roundabout on South Cedar Avenue connecting to a realigned Broad Street and a relocated North Oak Avenue
Wheaton called it "this transformational, legacy project" that would keep "revitalizing our WestSide while creating opportunities for future generations." What the same coverage did not include, as of that July report, was an actual construction start date. The plan had grown from a parking lot into a five-acre public park concept, and a construction calendar for the larger scope had not yet been announced.
Here is what that means laid side by side:
| What | Status | Where |
|---|---|---|
| Chill Billy's Lounge | Open since October 2025 | 102 N Cedar Ave |
| Westside Luxuries | Open, grand opening covered August 2026 | 149 W Spring St |
| 39 Depot parking lot | Originally targeted for Q1 2026 groundbreaking | Depot St & S Cedar Ave |
| 39 Depot road improvements & roundabout | Originally targeted before end of Q3 2026 | Cedar Ave & Broad St |
Two local businesses are open and serving customers. The city's project for the surrounding area has a larger vision than it started with, and as of its most recent public update in July 2026, a groundbreaking date had not been announced.
Not Every New Opening This Year Is Downtown
The WestSide is not the only part of Cookeville turning over its storefronts. The Upper Cumberland Business Journal reported that the IHOP off Interstate Drive, at 1115 Interstate Drive, is closing after the property sold to Verlaine Capital in an all-cash deal covering both the land and the building. Employees were told the closure would happen quickly. First Watch, the national breakfast, brunch and lunch chain, has already listed that same address as an upcoming location on its own site, complete with opening week extras: a free pot of its Project Sunrise coffee, a free tumbler for the first 100 guests, and a Friends and Family Pre-Opening Event ahead of the public debut.
First Watch is not a small operator testing a market. The company reported 648 restaurants across 32 states as of the end of the first quarter of 2026 and has said it plans to add 59 to 63 net new restaurants system-wide during the year. Newsweek named it the No. 1 breakfast chain in recent rankings. Its arrival on Interstate Drive is a different kind of story from Chill Billy's or Westside Luxuries, a national chain filling a national-chain-shaped hole rather than an independent concept finding a home. But it lands in the same calendar year, which says something about how much of Cookeville's food and retail map is moving at once.
What This Actually Tells a WestSide Regular
If you already eat, shop or walk through the WestSide, the practical read is simple. The businesses that make the neighborhood feel different are already open and taking customers. The construction that will eventually reshape the same streets, the roundabout at Cedar and Broad, the new green space, the parking that replaces street parking, has a stated ambition but no confirmed start date as of the most recent public reporting in July 2026. Plan an evening at Chill Billy's or an afternoon browsing Westside Luxuries without waiting on the city's timeline. The eventual construction, whenever it starts, will change how you get there before it changes what's there to see.
If you're curious about what any of this means for property nearby, or just want a second set of eyes on how the WestSide's changes might affect a future move, Leslie Scott is always glad to talk it through, no pressure attached.
