A Taste of Fall in Southern Indiana

THIS ITINERARY AT A GLANCE

Step into Southern Indiana’s fall charm, where historic river towns meet sweet traditions, steamboat history and rolling wine country. Over three days, you’ll sample handcrafted candies, stroll fossil beds older than dinosaurs, and toast the season in Starlight’s vineyards all while soaking up the warmth of Hoosier hospitality.

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Enjoy These Attractions and More:

Culbertson Mansion State Historic Site
Union Game Yard
Howard Steamboat Museum
Huber’s Orchard, Winery & Starlight Distillery
Downtown New Albany

Day-to-Day Southern Indiana Itinerary

DAY 1: Historic Charm & Sw eet Traditions

Begin your autumn escape in New Albany with a guided tour of the Culbertson Mansion State Historic Site. Built in 1867, this Victorian showpiece brims with ornate woodwork, elaborate frescoes, and stories of one of Indiana’s most prominent families. It has over 20 rooms and sits next to the Ohio River.

By midday, move your way up the river to Jeffersonville and step into Schimpff’s Confectionery. Experience a live candy-making demo to start your visit with the hypnotic swirl of molten sugar. Then, go for a stroll through the attached candy museum brimming with vintage delights and a generous dash of sweet nostalgia.

Lunch is pure fun at Union Game Yard, an indoor-outdoor playground for all ages with yard games and casual eats. It is the perfect setting for larger groups. Afterward, tap into your creative side at Pinot’s Palette, painting and sipping your way through an instructor-led art session that’s as much about laughter as it is about brushstrokes.

The day wraps in Clarksville at Derby Dinner Playhouse, where a hearty buffet and a Broadway-style musical make for an ideal all-in-one night of entertainment. A perfect finale to a standout first day.

DAY 2: Steamboats, Fossils & Local Flavor

Start your morning at the Howard Steamboat Museum in Jeffersonville, where a Victorian mansion houses intricate models, artifacts, and the legacy of America’s steamboat era.

Then head to Falls of the Ohio State Park in Clarksville to marvel at the world’s largest exposed Devonian fossil beds, a 390-million-year-old prehistoric timeline etched in stone along the riverbank.

For lunch, relax with riverside views at Upland Brewing Company, where seasonal craft beers pair beautifully with hearty pub fare.

In the afternoon, explore The Floyd County Carnegie Library Cultural Arts Center in New Albany. Admission is free, but the cultural insights are rich, from regional art to exhibits on the Underground Railroad and Civil War. The rotating galleries ensure there’s always something new to discover with each visit.

The evening’s grand finale is at MESA: A Live Dining Show. Watch as local chefs prepare each course before your eyes, weaving culinary stories between bites for a truly interactive dining experience.

DAY 3: Wine Country Farewell

To start your third day, visit a 600-acre farm, Huber’s Orchard, Winery & Starlight Distillery, where group tours showcase vineyards, distilling rooms, and tasting flights that span from sweet wines to small-batch bourbon. Stroll the farm market for seasonal produce, gourmet treats, and house-made jams.

Lunch is a Southern Indiana classic at Joe Huber’s Family Farm & Restaurant with platters of crispy fried chicken, garden-fresh vegetables, and desserts that taste like grandma’s kitchen.

Spend the afternoon enjoying optional seasonal activities at the farms or return to downtown New Albany for last-minute shopping before you depart.