I’ve been privileged to spend a lot of time in small Southern towns riddled with charming historic downtowns and the friendliest locals you ever did meet. But with that often comes a pattern – a few local spots barely holding on, and chains and corporations creeping in seemingly by the second.
When I visited Shelbyville, Kentucky, I was pleased to find a complete deviation from the latter part of small-town Americana. I sauntered down that adorable Main Street doing double-takes – that vintage clothing store was started by a local kid when he was 19 years old. That hat shop? A milliner creating 600+ custom pieces a year. The cheese shop, the boutique, the coffee shop… all are locally owned, and many by young entrepreneurs who chose to build something in their own towns rather than fleeing to bigger cities.
So if your 2026 travel plans can include supporting a small town with locally owned, independently run businesses in charming small towns, have we got the guide for you.
Here’s a small sample of the spots to check out during your visit to Shelbyville.
Shelby Vintage
When I was 19, I was angsty and skipping my morning classes. When Braden Roberts was 19, he started what would become Shelby Vintage, a super cool collection of pre-1990s apparel. The brand amassed a social media following that brought people to town to dig through his inventory, and soon after opening his first brick-and-mortar, he moved into a larger storefront just down the street in downtown Shelbyville.
Wakefield-Scearce Galleries at Science Hill
This American Dream story dates back to 1825 when Julia Tevis did something unprecedented: she opened Science Hill Female Academy based on the belief that girls were just as capable as boys in science, math, and chemistry. Gasp! For 114 years, it was one of the most respected female boarding schools in the country, attracting students from across America to study in what was then the Kentucky wilderness.
In 1947, Mark Wakefield and Mark Scearce leased the old chapel to sell English antiques, and eventually took over the entire space. Today, the Wakefield-Scearce Galleries span 35,000 square feet, transforming the classrooms, dorms, courtyards, and more into an enthralling destination for appreciators of art, history, antiques, and beautiful things in general. When silver was rationed during World War II, Mark Scearce had to pivot his jewelry business and started creating his own handmade sterling silver mint julep cups. They’re iconic, recognizable, and available for purchase onsite today (and, if you take a “behind the scenes” tour, you can peek into the silver vault).
If you time your visit to Shelbyville for Christmas (highly recommend), the gallery transforms into 30+ themed rooms of holiday displays that take months to prepare, and the gifting opportunities are, obviously, endless.
Something Cheesy
I believe I was a mouse in a former life given my obsession with all things dairy, so the Shelby County tourism team knew exactly what they were doing when they brought me to Something Cheesy.
The downtown shop is owned by Claire Kelly, with her husband Bill providing tech support and their dog Nikolai handling quality control via cheese tax collection (where do I submit my resume?). This female-owned business was built on a passion for clean eating, offering non-GMO products sourced in the United States, and promoting a healthier society—all while celebrating really good cheese.
In true small-town fashion, they’ve partnered with the community theater across the street so that you can grab a to-go charcuterie cup before the show or during intermission.
The Polkadotted Pineapple
We’ve written about Dori Lewis before on Modern South, so when I met her in person at The Polkadotted Pineapple, I was a little starstruck. We chatted for a bit before I put my blinders on to bypass the rows of cute blouses and coats on a mission to stare at her handiwork: dozens of hats in various stages of completion were displayed across the back of the shop—feathers and colors galore exploded in a delightful feast for the eyes.
Dori is a modern-day milliner who creates more than 600 headpieces annually from her brick-and-mortar shop on Main Street, many for the Kentucky Derby. What started as a hobby making hats for friends became a real business that’s keeping Kentucky’s millinery tradition alive in Shelbyville. You can buy ready-made hats or book an appointment for a custom piece at the Polkadotted Pineapple.
Sixth & Main Coffeehouse
The building (a former drug store) has been standing since around 1860, but Sixth & Main has been serving downtown Shelbyville since 2005. They roast their own coffee twice a day, and if you time your stroll down Main Street just right, you can smell it wafting into the street.
I stopped in for an afternoon iced latte and found everything you’d want from a locally-owned coffee shop: local art on display, new and used books available for purchase, a friendly barista, and a few locals typing away productively before quittin’ time.
This article is presented in partnership with Visit ShelbyKY, a Modern South Founding Partner.
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