A family-owned Mexican restaurant chain has planted its flag on Winchester's busiest retail strip, filling a long-vacant Frisch's Big Boy building with fajita-sized chimichangas, bourbon margaritas, and a bar designed to be the room's centerpiece. Pepper's Mexican Grill held its official ribbon-cutting ceremony at 843 Bypass Road on Wednesday morning, marking the sixth location owner Octavio Correa now oversees across Kentucky.
The Winchester-Clark County Chamber of Commerce organized and hosted the ceremony at 10:45 a.m. on Wednesday, October 7, according to the Winchester Sun. Chamber members turned out for the occasion, and Correa, who has spent about eight years in the restaurant business, told the paper simply, “We've been doing pretty good.”
The building itself carries its own local history. The 5,799-square-foot property sits on a 1.03-acre parcel and previously housed a Frisch's Big Boy before that restaurant's permanent closure, according to a CityFeet commercial listing. The spot sits along Winchester's primary retail corridor, near anchors like Kroger, Walmart, and Lowe's, making it one of the busiest commercial stretches in Clark County.
A Menu Built Around Simplicity and a Six-Year-Old's Approval
Pepper's serves Mexican staples including fajita-sized chimichangas, tortas, street tacos, and street corn, with roughly 20 lunch plates on the menu, per the Winchester Sun's reporting. “We do have some hidden Mexican dishes, but for the most part, it is more geared towards, like, the fajita-sized chimichangas,” Correa said. Asked what to order, he recommended the street tacos, tacos carne asada, and a margarita.
Even the restaurant's name reflects that straightforward approach — Pepper's was chosen for its simplicity and kid appeal, a detail that resonates with Correa personally since he has a six-year-old daughter. The business is family-owned and operated, and Correa and his wife personally handle complaints, bad reviews, and catering orders, the Winchester Sun reported.
Bourbon Margaritas Take Center Stage at the Bar
True to Kentucky form, the bar is designed as the restaurant's centerpiece, stocked with a wide selection of bourbons feeding into the chain's signature bourbon margaritas. “We decided to make the bar kind of like a centerpiece,” Correa said. Multiple televisions will carry local sports, including University of Kentucky games, for diners who want to watch while they eat.
Beyond the bourbon margaritas, Pepper's Mexican Grill offers house-made aguas frescas, soft-serve margaritas, and specialty cocktails like the Cincy Red-Rita at its Kentucky locations. The chain's bourbon-forward bar concept has drawn enough attention that its Shelbyville location on Midland Trail is featured in official Kentucky Tourism materials as a casual dining stop near stops on the Kentucky Bourbon Trail.
Part of a Steady Multi-County Expansion
Winchester is the latest stop in what has become a deliberate regional growth strategy rather than a one-off venture. Pepper's now operates active locations in Cold Spring, Lexington's Hartland Parkway, Nicholasville, Shelbyville, and Dry Ridge, alongside the new Winchester restaurant. The Dry Ridge location, at 1000 Fashion Ridge Road, had its own ribbon cutting hosted by the Grant County Chamber of Commerce & Economic Development on November 10, 2025 — less than a year before the Winchester opening.
The chain's track record on food safety offers some operational context for the new location. Inspection records from the Lexington-Fayette County Health Department show the sister restaurant on Hartland Parkway earned regular scores between 92 and 96 during 2024 and 2025.
Community Giving on the Horizon
Pepper's plans to continue community work in Winchester similar to what it does elsewhere, including Dine to Donate fundraisers that return 10 to 15 percent of sales to local causes, shelter meal coupons, and support for schools and hospitals. Those community initiatives are expected to launch once the new location settles down, the Winchester Sun reported.
Winchester, the county seat of Clark County within the Lexington-Fayette Metropolitan Statistical Area, had a population of 19,134 at the 2020 census, according to figures cited by the ERI Economic Research Institute. Manufacturing remains the county's dominant industry, accounting for about 31 percent of local jobs and 36 percent of total wages, according to City of Winchester economic profile data — a workforce base that now has a new lunch option with a fully stocked bourbon bar. Pepper's Mexican Grill is located at 843 Bypass Road, with menu and location details available at peppersmexky.com or by phone at 859-355-5236.
