Summer Road Trips: Midwestern Wine Trails

The call of the open road is as booming as ever. As far as domestic leisure travel is concerned, more Americans are opting to go by way of the automobile. Whether it’s due to the flexibility of packing heavy and stopping at will along the way or the nostalgia of highway getaways, road trips are back! The Summer Road Trips series offers destinations for the perfect American road trip.

The popularity of artisan beverages has led to an explosion of wineries across the country in recent years. While California is still the king of wine production here in the States, there are plenty of wine trails in the Midwest that can give you the Sonoma experience in the Heartland.

Lake Erie Trail (Ohio)

The moderating lake effect has made the region from Toledo to Buffalo a prime wine-growing spot since the 19th century. Visitors can enjoy a covered bridge driving tour across northern Ohio while stopping in at a variety of wineries, from the giant Debonné Vineyards to the quaint yet acclaimed Markko Vineyard.

Markko Vineyard

Door County Trail (Wisconsin)

In Wisconsin’s Lake Michigan peninsula, eight wineries make up the Door County Wine Trail that takes visitors through the “Cape Cod of the Midwest.” Boasting the same latitudinal planes as the wine regions of Burgundy and Bordeaux, Door County’s established wine scene offers traditional varietals as well as sweet fruit wines to accommodate every palate. Visitors can be sure to stay active and entertained given the peninsula’s reputation for hospitality.

House and a light house
Canal Station Lighthouse, Photo by Greg Tally

Uplands Trail (Indiana)

Since the 1960s, winemaking on the plateau of south central Indiana has taken off. The Uplands Trail, stretching from Brown County to Bloomington to French Lick, features the nationally ranked Oliver Winery and Vineyards, a destination for fruit wines like Apple Pie, Cherry Cobbler, and Blueberry Moscato. The historic West Baden Springs and the Hoosier National Forest provide sundry excursions for this route.

A vinyard at sunset
Oliver Winery’s Creekbend Vineyard

Shawnee Hills Trail (Illinois)

Eleven wineries sit in the Shawnee Hills of southern Illinois, where limestone and sandstone formations tower over the rolling hills of a burgeoning wine industry. In 25 miles, the trail passes through small towns and the Shawnee National Forest, boasting quaint B&Bs, fall color, and — of course — wine. Blue Sky Vineyard offers a Tuscan setting and estate-grown vino, and Von Jakob houses a brewery as well as a winery.

Garden of the Gods
Garden of the Gods in Shawnee National Forest

Hermann Trail (Missouri)

Along the Missouri River, six family-owned wineries make up the Hermann Trail near the German town of Hermann. The Adam Puchta Winery bills itself as the oldest continuously-owned family winery in the country; the current owner is a seventh generation winemaker. Two miles north of Hermann is the Katy Trail, the nation’s longest rails-to-trails project at 240 miles.

Photo of Harmann, Missouri. Shows streets, homes, and trees
Hermann, Missouri, Photo by Dave Keiser

Glacial Hills Trail (Kansas)

Outside of Topeka and Lawrence, four family-owned wineries take advantage of the rich prairie soil created by receding glaciers in the area. A quiet Kansas getaway can include an affordable stay at the Crescent Moon Winery or Jefferson Hill Vineyards, and a day boating or hiking at nearby Perry Lake.

Lake side
Crescent Moon Winery

Loess Hills Trail (Iowa)

The silty hills of western Iowa were formed by sand-blown deposits toward the end of the last ice age. While loess soil is common in North America, nowhere is it deeper than in this special grape-growing region. All nine of the trail’s participating wineries commit to sustainable practices for producing wine from the delicate soils of the region. The Loess Hills Scenic Byway twists up through the unique landscape and past the wine destinations.

Green hills and woods
Photo by Billy Bluejay


Viking lore is at the heart of the Skål Crawl in lake-rich central Minnesota. The short trail includes a winery, a brewery, and a whiskey distillery near historic Alexandria. Small groups can imbibe Minnesotan beverages and visit Big Ole, the tallest Viking statue in North America, and the Runestone Museum, a tribute to the mythological Scandinavian history of Minnesota.

Skål Crawl logo

Nights in a Tree House

Spending a night in a tree house is one of those irresistible holdovers from childhood; we dream of drowsing off to the low drone of a zillion insects in the surrounding forest, waves of sound lifting into a crescendo and then slowly subsiding. My grandfather called them katydids. My college friend Donna Hunt, who was sharing my rented tree house — lodged in a 200-year-old white oak in the middle of southern Illinois’ Shawnee National Forest — immediately got out her iPad, Googled “katydid,” and quoted the Encyclopaedia Britannica: “Any of numerous predominantly nocturnal insects related to crickets and grasshoppers and noted for their loud mating calls.” A sexual evensong, all those katydid body parts rubbing madly against each other.

We chose this particular tree house because Donna’s daughter and son-in-law, Elizabeth and Marty Canfarelli, decided to build Timber Ridge Outpost and Cabins — a scattering of log cabins and tree houses — pretty much smack in the middle of the Shawnee National Forest. (Elizabeth’s card reads, 37°33’52.18″N, 88°20’17.03″W.) We chose the larger tree house — sleeps six, shower, air conditioning, kitchen, Wi-Fi: all very luxe. Ideal for travelers like ourselves who are beyond roughing it.

Donna and I became friends at the University of Illinois in the 1950s. We were outliers of a sort, being among the minority to come from the mostly rural southern part of the state. We are Californians now, neighbors by chance and luck, and one day last summer we found ourselves hankering for a visit to the place our folks always called “down home.”

We flew to St. Louis, slipped into a rented lipstick-red convertible, drove across the river to Illinois, and moved onto roads that seemed like one long tunnel of corn. The sky was blue, the air warm, the top down.

The U.S. Census Bureau’s most recent data show that Hardin County, home to the tree houses, had a population of 4,226 in 2014, many of them from families established in these hills and hollows for generations. At the local school, Elizabeth told us, every classroom has at least one set of cousins, sometimes two. Whenever land comes up for sale, the U.S. government makes an offer and adds another piece to the puzzle that is 280,000 acres of Shawnee Forest. There is not a single stoplight in Hardin County; traffic scarcely exists, except for the oversized silver trucks that move in a loop all day and all night, taking coal from the nearby mines to the river and dumping it into giant barges.

The Shawnee National Forest covers much of the bottom tip of Illinois. The state is mostly flatland, except for a sector bordering Kentucky where the earth buckles into rolling hills with ridges and hollows. From the top of one of those hills, you can see for miles, no major highway in sight. Only forest interrupted occasionally by a clearing with a farmhouse and a hay field. Easy to imagine how it would have looked to those early arrivals who rafted down the Ohio to settle this country. One of them, John James Audubon, had a mill 60 miles upriver in Henderson, Kentucky. In 1809, he drew a Cooper’s hawk from these forests, and in 1813, a dickcissel. He might even have brushed past our white oak in his search for the birds immortalized in his masterpiece Birds of America. The winter of 1838 and ’39, the Cherokees from the Great Smoky Mountains paused in this hill country as they were pushed west, marking their trail with tears. Not too long after, my great-grandfather Brinker arrived from Germany, still wearing his wooden shoes.

Waking early enough to watch a midnight-blue sky turn pearl gray, then splashed with lavender, and finally full light laced with birdsong is high on my list of worldly delights.

Those pioneering days of river travel are long gone, leaving behind rusty little towns surviving as clusters of antique shops. You could make a case for there not being a whole lot more to do in this neck of the woods today than in Audubon’s time: birding and hunting and hiking, and horseback riding on trails that move up and over and through the woods.

In Abraham Lincoln’s day (he was a Kentucky boy before he came to Illinois), telling stories took the place of radio and television. Abe was a master of the tall tale; Marty Canfarelli carries on the tradition. Get him going on hunting licenses, bobcats, and road kill, or ask his wife Elizabeth about her hermaphrodite cat. Then talk to us about laughing until your side aches.

There are lakes for swimming and small car ferries that wobble across the Ohio River, delivering travelers to Kentucky. When we booked our tree house, we were told to bring our own provisions, all grocery stores being out of range of Timber Ridge. But we also knew we would talk Elizabeth into taking the wheel of the red convertible to drive us onto one of those quavering car ferries and into Kentucky, where the Amish have settled.

Across the river, tacked to a tree or a post in front of almost every farm was a sign announcing what was available that day: fresh bread, ripe tomatoes, green beans, and sweet corn. At a stall served by a shy young Amish girl wearing a long gray dress and a delicate, starched white cap, ears of corn were piled on a cart. We tested one ear by pulling back a few leaves to find a fat little worm noshing on the tip end. Pesticide free. We flicked the little pest off and checked to find the rest of the ear unblemished. At another stop, we found peaches from a local orchard. We bought a peck. Peaches for breakfast in a tree house, and later sweet corn, green beans, ripe tomatoes for dinner, and, of course, peaches again for dessert.

Our tree house required climbing 20 stairsteps to the main cabin; inside was a ladder to a loft big enough for two queen-sized beds. Donna climbed the ladder and chose the bed next to a tree trunk that moved into the room, up, and out again. I chose the pullout sofa in the living room, where I could look out the window at a night sky slathered with stars. There was no swaying in this solid treehouse — for that, you choose the smaller one, purposely built to move in the wind — but from my nighttime perch there was the illusion of rocking, created, I think, by the rustle of all those oak leaves in the slightest breeze, and maybe a little moan or two from creaking branches.

Sleeping in the tree house — and waking early enough to watch a midnight-blue sky turn pearl gray, then splashed with lavender, and finally full light laced with birdsong — is high on my list of worldly delights. Still higher is the momentous deck just outside the screen door. A platform, it wraps around the very heart of the massive tree, placing you up there with the squirrels and birds and other tree lodgers. A singular world with a table for eating, chairs for reading, tree time. Donna and Elizabeth had trouble dislodging me long enough to drive over to the famous Museum of the American Quilter’s Society, across the Ohio River in Paducah, Kentucky, a must-see for anyone who values the art and the craft of quilting, which includes all of the women in the generations of my family who once lived nearby.

On the way to the museum, just before we crossed the river, we passed a turnoff for Brookport, Illinois, where my mother went to high school. The schoolrooms in this county still have students named Brinker and Douglas and Kerr, the current generation of my kin — descended from the aunts and uncles and cousins who stayed to make their lives here. Kids who, maybe, spend the early evenings on front porches with their granddads, listening to the katydids.