Amazing Midwest Wine Trails to Explore This Summer

May 27, 2025

This weather has us thinking about basking in the late evening sun, sipping on a crisp, fresh glass of wine harvested right here in the Midwest. That’s right, folks, you don’t need to travel to the West Coast or to Europe to sample some of the finest vintages of vino. The midwest is home to quite the variety of wineries and vineyards, and our climate in this region gives us a unique advantage to growing some of the finest grapes around.

Today on the blog, we’re sharing our picks for great midwest wineries and wine trails to explore. We recommend utilizing these as a springboard for a 4 day weekend road trip, as you travel and experience all the local regions have to offer, and sample unique wines and beverages. It’s the perfect time to plan a romantic summer getaway with someone special. So what are you waiting for? Hop in your new car from classic and you’ll be well on your way to enjoying a romantic sunset with some rose or perhaps a few mimosas over brunch in the summer breeze!

The Shawnee Hills Wine Trail in Illinois features 11 award-winning wineries, including some of the state’s oldest and most celebrated! While these wineries are shining stars in the region, there are more than 100 wineries and 450 vineyards, making our home state the 12th largest wine producing state in the US. This 40-mile trail will take you through the scenic route introducing you to plenty of charming towns with wonderful eateries, shops, boutiques, and galleries to explore as well.

The Heart of Illinois Wine Trail takes enthusiasts through 9 central Illinois wineries, celebrating that homegrown, hometown feel of the region. You’ll stop by Lewistown, Galesburg, Oakford, Mackinaw, Canton, Washington, and Petersburg. Ask any winery how to get your Wine Trail Passport and a list of giveaways and special events!

The Indiana Uplands Wine Trail features 9 different wineries across central Indiana for a one-of-a-kind experience. You’ll sample the finest wines there are to be found in the nearly 5,000 square mile grape-growing region called the Indiana Uplands Wine Country. Learn about the history of the land, how wine-making came to the area, and what makes it the perfect place to cultivate grapes!

The Driftless Wine and Cheese Trail in Wisconsin takes visitors on a tour through 7 wineries and 7 cheese producers, for a total of 14 exciting culinary destinations. The trail aims to showcase the best of the best in Wisconsin’s history and agricultural treasures! Meet local business owners and family run vineyards and creameries and learn about the history of the region’s wine making, cheese mongering, and passion for local eats. (Wine and cheese are of course included!) It’s a great way to delve into local history and celebrate this iconic Midwest region.

Wine and cheese served for a friendly party in a bar or a restaurant.

The Old Mission Peninsula Wine Trail in Michigan features 10 wineries with a diverse range of flavors and profiles you won’t find anywhere else. You’ll experience some of the most breathtaking views along Grand Traverse Bay, and the unparalleled beauty of the Old Mission Peninsula region. Visit during the spring and summer months and you’ll be treated to a wide selection of live events, special tastings, and limited engagements. Plus, the region is also known to be home of the Brys Estate and their sprawling lavender garden, featuring more than 6.000 lavender plants and shrubs.

The Leelanu Peninsula Wine Trail is just a hop, skip, and a jump away from Old Mission, and brings you 20 more award winning vineyards and wineries! Along the way you’ll experience that small town charm with quaint little towns and villages offering lots of unique shopping and eateries. If nature is what you’re after, you’ll find an abundance along the drive featuring sprawling vineyards, farms, and forestlands, as well as at the wineries themselves with lush, verdant hills. It’s no wonder that it’s become one of the top destinations in the Midwest for wine enthusiasts.