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 a winemaking hobby in the 1960s, Oliver Winery officially started in 1972, making it over half a century old. The winery is 100% employee-owned, and went through a $12.6 million expansion that began in 2023. It took the number two spot for Best Tasting Room in Newsweek's Readers' Choice Awards in 2026, and made Travel + Leisure's top 25 wineries in 2017. The winery specializes in fruit wines, though they have a wide variety, as well as a large tasting room full of rustic charm, as well as extensive grounds and gardens where you can have 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 has a best customer service in the midwest award, so you can have a relaxing trip from start to finish. 

When university law professor William Oliver started winemaking and decided to turn it into a business in the early 1970s, he helped pass legislation to create small Indiana wineries. It went through the year before the winery opened. The 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. It's 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.

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. These take you around the grounds, and into the production area, as well as giving you wine to taste. 

Additionally, you can reserve a picnic on the patio. You'll get a two-hour window, as well as a picnic basket with dried fruits, meats, and cheeses, as well as 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. However, you can stop by the tasting room and take your wine and a picnic to the garden grounds. They have picnic tables as well as plenty of space for you to lay out a blanket. The landscaped grounds themselves are stunning, with stone sculptures, flowers everywhere, and a pretty pond and waterfall (above). 

There are events through 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.