8 Midwest Wine Trails Featuring Charming Small Towns and Scenic Views

Vineyard roots run deep across the region, with smaller, boutique wineries crafting vintages that very often punch above their weight when it comes to variety, quality and taste. Hopping on a wine trail is a convenient and fun way for wine-lovers to try offerings from several different wineries, and the nation's midsection has some stellar, scenic routes well worth checking out. Here are eight wine trails to explore in the Midwest, plus recommendations to make the most of your trip.

Driftless Wine and Cheese Trail, Wisconsin

In a state that produces more than 600 types of cheese, there are plenty of opportunities to sample it all across Wisconsin. And what could pair better with locally crafted fromage than a glass or two of locally produced wine? You'll find both along the Driftless Wisconsin Wine and Cheese Trail in the southwestern portion of the state. Be sure to stop and shop at Carr Valley Cheese, known for their awards (more than 850!) and perfect curds. When you've polished off your squeakers, head to Wollersheim Winery and Distillery. This historic spot overlooking the Wisconsin River offers tours as well as tastings of their wines and distilled spirits, including high-proof absinthe for the bravest in your group!

Great River Road Wine Trail, Iowa, Minnesota and Wisconsin

Featuring eight wineries spread across three states, the Great River Road Wine Trail treats guests to excellent vintages and incredible views of the Mississippi River, plus it swings through some sweet, smaller towns. Garvin Heights Vineyards, set into the bluffs just outside the city limits of Winona, Minnesota, makes a variety of reds, whites, roses and blends on-site. If you want to combine your wine experience with America's favorite pastime (baseball), hit up DnA Vintners in La Crosse, Wisconsin, famed for its cranberry wine. Afterward, walk a block away to the Lumberyard, where the La Crosse Loggers play during the summer. The baseball team is part of the Northwoods League, featuring some of the country's top college athletes.

Hermann Wine Trail, Missouri

Perched in the limestone bluffs above the Missouri River just 90 minutes west of St. Louis, Hermann was founded by German immigrants who settled the land because it reminded them of the Rhine River valley. When immigrants arrived in the 1840s, planting vineyards was one of their first orders of business. The tradition was literally stomped out during Prohibition—plants were uprooted and destroyed—but revived in the 1970s. Today, visitors can check out seven family-owned wineries along the Hermann Wine Trail and delight in the town's red-brick charm. Those seeking a little more adventure might consider renting a bike and cruising the nearby Katy Trail, a former railroad route turned into a flat, 240-mile trail that crosses through the heart of the state.

Lake Erie Shores and Islands Wine Trail, Ohio

Northern Ohio's shoreline along Lake Erie provides the ideal microclimate for growing grapes. Rieslings and Chardonnays especially love the lake breezes and cooler temps, so you'll see plenty of each variety at the 18 wineries along the Lake Erie Shores and Islands Wine Trail. And you can't beat the lakeside views. Be sure to check out the "wine islands'' just north of Sandusky; Crooked Tree on Kelleys Island is especially photogenic. Try their Raccoon Red, a Cabernet Franc/Chambourcin blend named for the creatures who occasionally head to the vineyards for a sweet snack once the sugar level rises in the grapes.

Loess Hills District Wine Trail, Iowa

An hour outside Omaha, the rolling hills of western Iowa were formed toward the end of the last ice age by sand-blown deposits. These hills are made of soft, crumbly sediment called loess (rhymes with bus). The deep soil along the Loess Hills District Wine Trail allows vine roots to grow long and strong into the ground. The hills lend a beautiful backdrop for wine-sipping. The Loess Hills National Scenic Byway passes wineries like Prairie Crossing, which uses lesser-known Iowa-grown grapes including Frontenac, St. Croix and Brianna in its wines.

Old Mission Peninsula Wine Trail, Michigan

With its miles of shoreline along Grand Traverse Bay, charming towns and acres of cherry orchards, the Traverse City area has long been a family-favorite destination. But wine-lovers know there's also something fabulous waiting for them, too. With 10 wineries featuring a vast array of varietals, the Old Mission Peninsula Wine Trail is an experience you'll want to add to your Traverse itinerary. Many of Old Mission's wineries offer comfortable and convenient on-site lodging, making it easy to stay the evening after a day of sampling. Be sure to check out Brys Estate's secret garden, a dozen acres with more than 6,000 lavender bushes. When you're done wandering, stock up on lavender-based products including lotions, lip balms and even ice cream in the gift shop. If you're visiting Old Mission during the warmer months, take a beach break. Haserot is a favorite with locals and visitors alike. (And if you're looking for more wine destinations, the Leelanau Peninsula Wine Trail is just a hop away.)

Shawnee Hills Wine Trail, Illinois

Eleven wineries in charming small towns dot the highways in and around the Shawnee National Forest in southern Illinois, delighting both wine-lovers and outdoor enthusiasts. Take breaks from hiking, biking and exploring by sipping and sampling the locally grown vintages at wineries like award-winning Blue Sky Vineyard along the Shawnee Hills Wine Trail. About 40 miles east, active adventurers can easily hike the quarter-mile observation trail at the Garden of the Gods, take in the vistas and towering rock formations, then reward themselves with an afternoon of wine sampling and an overnight stay.

Fun fact: The Shawnee Hills trail is on the path of totality for the total solar eclipse taking place on April 8, 2024. Visitors can expect more than 4 minutes of darkness, and accommodations are already booking up for the out-of-this-world event!

Uplands Wine Trail, Indiana

In south-central Indiana, nine wineries comprise the Indiana Uplands Wine Trail. In a landscape of rolling hills and rocky outcrops, the soil here is conducive for grape growth—in fact, the Indiana Uplands has been the epicenter of the state's wine production for more than 170 years. The Huber family started planting vineyards in the 1840s. After Prohibition was abolished, the Hubers replanted the grapes and eventually founded Huber Winery (the family's seventh generation still works the vines). Love rose? Try Huber's Stella di Luce, a dry, Spanish-style rosado.

For a German-style wine experience, include a stop at Winzerwald. Its fruit wine offerings include blueberry, cherry and peach, plus German favorites Riesling and Gewürztraminer. (We recommend going all out and pairing your tasting with a giant Bavarian-style pretzel.)