Discover seamless itineraries featuring Broadway-style theater, award-winning estate wines, and interactive art in Clark and Floyd counties
Step into Southern Indiana’s fall charm, where historic river towns meet sweet traditions, steamboat history, and rolling wine country, offering a mix of top-tier entertainment and agricultural heritage. From the performances at Derby Dinner Playhouse and the tastes at Huber’s Orchard & Winery to the creativity at Pinot’s Palette, the region provides diverse, easy-to-plan experiences. Here are some top attractions in this beautiful part of the country.
Derby Dinner Mamma Mia! Cast standing on stage
Derby Dinner Playhouse
Groups can enjoy an unforgettable night out at Derby Dinner Playhouse in Clarksville, one of the nation’s oldest and largest continually operating professional dinner theatres. Each performance includes a delicious buffet meal and live Broadway-style entertainment, making it a convenient all-in-one group experience. With year-round productions ranging from musicals to comedies, there’s a show for every audience to enjoy.
Located just minutes from downtown Louisville, Kentucky, this 450-seat theatre, which has been going strong for more than 50 years, is noted for its professional productions of Broadway musicals, comedies, and Children’s Theatre.
The Derby Dinner stage is surrounded by tiers of dining tables set “in-the-round,” which provides an intimate setting not usually found in most theatrical venues. A freshly prepared home-style buffet includes such Southern favorites as fried chicken and fish, green beans, mashed potatoes, and a full salad bar. And homemade desserts are a specialty of the house.
Huber’s Winery/Starlight Distillery
Sip and savor award-winning wine and spirits at Huber’s Orchard & Winery, Indiana’s largest estate grown winery, and Starlight Distillery in Borden. Groups can tour the grounds, winery, still and rick houses, learning about the grapes and grains grown on this 600-acre farm run by the same family for seven generations. Indulge in brunch, lunch, ice cream or goodies from the Farm Market.
Starlight Distillery is Indiana’s most award-winning, farm-to-bottle distillery. It has won a variety of awards, including Best Overall Bourbon in 2025, Best in Class Best Special Barrel-Finished Bourbon (2025), and Best in Class Best Craft Distiller Whiskey (2025). It’s easy for a group to spend the day there. This family-owned establishment features sustainably handcrafted spirits, a Huber family tradition since 1843.
Pinot’s Palette
Unleash your creativity at Pinot’s Palette in Jeffersonville. With a painting library of more than 3,000 designs, groups can choose from a wide variety of guided paint-and-sip creative activities, including stretched canvas, door hangers, painted wine glasses, bottle art, and more. Guests will leave with a one-of-a-kind souvenir and a memorable SoIN experience.
“Tour operators choose Southern Indiana because we make group travel easy. With diverse attractions, convenient access, customized itineraries, and hands-on destination support, SoIN delivers the experiences travelers want and the service planners need,” said Todd Read, Senior Tourism Manager, SoIN Tourism. “Our hospitality isn’t just a promise; it’s what defines every group visit. In SoIN, groups aren’t just visitors, they’re welcomed guests, and that commitment to service is what keeps them coming back year after year.”
