If you’ve been looking for an excuse to tour Southern Indiana’s wine country, here it is. For two weekends in February 2026, the Indiana Uplands Wine Trail transforms into a cocoa-infused paradise for its annual Chocolate Lover's Weekend.

Dates: February 7–8 and February 14–15, 2026 (Valentine’s Weekend).

• Location: Participating wineries along the Indiana Uplands Wine Trail.

• Tickets: No tickets or central registration required! The event is self-guided. You simply pay the tasting fees at each individual winery you choose to visit.

Each winery on the trail puts its own spin on the pairing. You’ll find everything from house-made truffles and chocolate-infused desserts to partnerships with legendary local candy makers like Schimpff’s Confectionery.

Because it’s self-guided, you can hit all nine wineries over four days, or just pick a few favorites for a relaxed afternoon.

The Participating Wineries (All 9 Stops)

Oliver Winery (Bloomington)

The largest on the trail. In 2026, they are celebrating "Chocolate Lover's Month" all through February. Look for their reserved "Truffles & Tastings" experience or book a private heated igloo for the ultimate romantic vibe.

Brown County Winery (Nashville)

Nestled in the heart of the village. Known for their cozy tasting room and specialty fruit wines that pair beautifully with dark chocolate.

While you're in town, explore the shops and trails; our Brown County travel guide has you covered.

Butler Winery (Bloomington)

A pioneer of Indiana wine. Their vineyard location offers a peaceful, rustic setting for a quiet date.

Owen Valley Winery (Spencer)

A true hidden gem. Their farm-to-table approach often extends to their chocolate pairings.

French Lick Winery (West Baden Springs)

Located right next to the historic resorts. They often feature chocolate-infused desserts and offer a full Italian-inspired menu if you need a lunch break.

Planning to make a weekend of it? Check out our French Lick travel guide for where to stay, eat, and explore beyond the winery.

Winzerwald Winery (Bristow)

Specializes in German-style wines. Expect unique pairings like chocolate with their signature spiced red wines.

Turtle Run Winery (Corydon)

Known for its complex, dry wines. It’s a favorite for "serious" wine lovers who want to see how a bold red stands up to high-quality cocoa.

Best Vineyards Winery & Distillery (Elizabeth)

If your partner prefers spirits, this is the stop for you. They offer wine and spirit tastings, often pairing their brandies with chocolate.

Huber's Orchard, Winery & Distillery (Starlight)

Huber's Orchard, Winery & Distillery (Starlight) A massive destination with over 600 acres of orchards and vineyards. For 2026, they're pairing their pours with Schimpff's chocolates in their Tasting Loft.

Read more about what makes Huber's a Southern Indiana staple.

Pro Route Ideas

The "North Loop" (Bloomington & Nashville): Perfect for a day trip from Indy. Start at Owen Valley, hit Oliver and Butler in Bloomington, and end with dinner and a stroll through Nashville.

The "South Loop" (Corydon & Starlight): Ideal for those coming from the Louisville area. Visit Huber’s, Best Vineyards, and Turtle Run for a concentrated afternoon of tasting.

The "Resort Weekend" (French Lick & Bristow): Book a room at the French Lick Springs Hotel and spend your weekend oscillating between the winery, the spa, and Winzerwald.

Tips for the Perfect Trip

Since Monday, February 16, 2026, is Presidents' Day, several wineries (including French Lick and Oliver) may extend their specials through the holiday.

Think Beyond Wine: Many of these locations, like Huber’s and Best Vineyards, have incredible distilleries on-site. If you’re "wined out," ask about their chocolate and bourbon/brandy pairings.

Looking for more vineyard destinations? Check out our full list of the best wineries in Indiana for year-round tasting adventures.