Events

Grape Stomping Competition: teams of 4, two rounds, one winner-take-all championship. Champions win a hot air balloon ride. $25/person or $100/team, 21+, includes wine and a souvenir glass. Only 8 team spots. Free to watch: live music 3-5pm, food trucks, wine specials. Rounds at 3:30, 4:30 and 5pm.

Tailgate Tastings is here! Enjoy five wines paired with five tailgate favorites at Oliver Winery, a seated, reserved experience with limited dates and availability. Fixed menu, no substitutions. Come hungry, come thirsty, bring your game face. Every taste is a win!

Cozy up, Bloomington — it's time to break out your best flannel and soak in leaf peeping at its finest. Flannels & Flights Weekend trades summer patio vibes for crackling fires, golden hillsides, and the coziest wine weekend of the season. The grounds are at peak fall color — the perfect backdrop for your best shot yet. Layer up, grab your flannel, and come find your golden hour. What's in Store Stroll the grounds for leaf peeping at its finest, with Southern Indiana's best fall color as your backdrop — bring your camera, because this is prime Instagram territory. Our Apple Pie Frosé is back, frozen, spiced, and made for sipping on a crisp fall afternoon. S'more season is here too, enjoyed two ways: settle in for our fan-favorite tableside s'mores, or grab a s'more kit to enjoy out on the grounds — fireside or fireside-adjacent, there's no wrong way to get your fix. Cool off with buckets of cider, on special and made for sharing while you soak in the color. And live music with Black Orchid sets the mood on the patio from 3–5pm for a perfect fall afternoon. Wear your coziest flannel, bring your people, and settle in for an afternoon built for crisp air, warm fires, and good wine.

Tiles & Tastings is back at Oliver Winery! Join Mahj in Bloom for two rounds of American Mahjong open play, wine in hand. Ticket includes a complimentary glass of Oliver wine. Not a lesson, players should know the rules and bring their own 2026 NMJL card. Grab your glass and let's Mahj!

Howl-O-Ween is back at Oliver Winery! Bring your pup for dog costume contests, local rescue meet-and-greets, and fall vibes among the vines. Free admission, costume contest requires advance sign-up. Leashes on, costumes ready, see you and your best friend there! Check back soon for more info on register your furry friend for our dog costume contest.