Indiana's Oldest And Largest Winery Has Rustic Charm And Stunning Outdoor Gardens

For people who tour wineries, the first U.S. destinations that probably come to mind are wine country in California and perhaps New York's Long Island. You're probably not thinking of the Midwest. However, you may want to change that. The breathtaking student city of Bloomington, Indiana, has some renowned wineries, including the state's oldest and largest, Oliver Winery.

Started by William Oliver, who took up winemaking as a hobby in the 1960s, Oliver Winery officially opened in 1972, making it over half a century old. A year before opening, Oliver helped pass legislation — The Indiana Small Winery Act — to make small Indiana wineries legal. Since then, the 54-acre winery has received a lot of recognition. It took the No. 2 spot for Best Tasting Room in Newsweek's Readers' Choice Awards in 2026, and made Travel + Leisure's top 25 wineries in 2017. Though the winery has a large variety of wines, it specializes in fruit-forward flavors that visitors can sample in its rustic tasting room or enjoy outdoors on its extensive grounds, complete with scenic gardens for a picnic. 

One reviewer on Tripadvisor, who tried the Blueberry Moscato, says of Oliver Winery, "We were blown away by the beauty of the property, and the staff was amazing. We were encouraged to bring in our own little picnic lunch of the Monday we visited. The grounds were just breathtaking with the fall colors ... " Bloomington is around 45 miles from Indianapolis International Airport, which received an award for best customer service in North America in 2023, so you can have a relaxing trip from start to finish. 

Today, the winery produces over 800,000 cases per year. Its first big hit was the Camelot Mead, made with orange-blossom honey, which is not only still on sale at the winery, but, according to the website, is the No. 1 selling honey wine in the country. They focus on fruit wines like their Blood Orange Spritz, Italian Lemon Spritz, Cherry Moscato, and Melon Mint Moscato. However, they also have semi-sweet, semi-dry, dry, and sparkling varietals.

Their charmingly decorated tasting room (above) has high, wooden-beamed ceilings, vine decorations, and pretty items for sale, with wine bottles lining the walls. The building itself looks like an upscale, but rustic barn. "I can't explain how much I love the grounds here," a reviewer raved on Yelp. "Stone archways and pathways, small waterfall, and the rustic country store look of the winery. Not to mention the views from the patio overlooking the pond." 

Visitors can also reserve a picnic on the patio. You'll get a two-hour window and a picnic basket with dried fruits, meats, cheeses, freshly-baked bread, and homemade garlic spread. You can drink the wine you purchase, and it can be delivered right to your table. They'll give you a price when you reserve. You'll also get a souvenir wine tumbler. Additionally, you can stop by the tasting room and take your wine and a picnic to the meticulously landscaped garden grounds. They have picnic tables as well as plenty of space for you to lay out a blanket. 

There is more to do at Oliver Winery beyond regular tastings. If you like to see the winemaking process from behind the scenes, there are tours you can reserve Friday through Sunday from April through October. You'll have wine to taste as you walk around the grounds and into the production area.

The winery is open daily outside of Thanksgiving, Christmas, and New Year's Day. (Hours are seasonal.) It's also wheelchair-accessible, and you can call for more details. They have a lovely covered patio that can be reserved. Kids and dogs are welcome on the grounds (though dogs can't visit the tasting room, patio, or production areas). You can do guided tastings, wine flights, and even pick up à la carte snacks and other items in the tasting room. On weekdays, you can book a guided tasting that lasts for an hour, and add on savory snack bites, keepsake glasses, and even enjoy seasonal-themed tastings.

Additionally, there are events throughout the year for guests to enjoy beyond the regular tastings and tours. For instance, at the time of this writing, there is a Truffles & Tastings experience where six wines are paired with local truffles in the winery's cellar, and private igloos outside with fairy lights where you can enjoy the wines. Finally, Bloomington, Indiana, is one of the most charming and walkable college towns in the Midwest, if you're looking to extend your vacation. The town also features another great wine-tasting spot, Butler Winery.