A Road Trip With Retro Charm—and a Car to Match; Want to upgrade your driving vacation? Rent a vintage car that suits the destination. To wheel around time-capsule towns in the midwest, writer Matthew Kronsberg sought out a 1960s woody wagon. Plus: Classic car rentals in Italy and the Cotswolds

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I'VE BEEN CALLED a lot of names in my life. More than once while I was behind the wheel of a car. This, however, was a first. The scene: my wife and I in a rental with my son, paused at a stop sign in a mellow residential Santa Cruz, Calif., neighborhood two blocks from the ocean. A guy on a bicycle comes bombing up behind us, and as he swerves past, lets fly a single-finger salute and a battle cry of "F--- you, moneybags!" Moneybags.

Thanks to some combination of dumb luck and dumber inventory management, the car-rental agency we'd visited two days before had upgraded us to a silver BMW 430i convertible. It was a hoot on the highway but a mismatch for the endearingly scruffy sensibilities of Santa Cruz. I found myself sinking low in my seat at stoplights, and was a little relieved when I returned it.

Most rental cars play bland supporting roles on road trips. If one calls attention to itself, it's usually for the wrong reason—a breakdown, an accident, distressing aromas blowing from the air conditioning or a ridiculous run-in like mine. I spent the flight home wondering what it would be like to take a trip where the car comes to the fore for the right reasons, where it heightens your experience, your connection to the landscape and to those who live there.

On a sunny Saturday morning a few weeks ago, I ventured into an industrial park just outside Minneapolis to find out. Morrie's Heritage, a small division of a large family of car dealerships, rents out vintage vehicles—frequently for wedding getaways but also for weekenders like me. Its soft-top '66 Ford Mustang was already gone when I arrived. Another customer was there with his nephew to rent a 1967 red Mustang fastback, in celebration of the latter's high-school graduation. I watched a young woman giddily examining the black 1969 Pontiac Firebird convertible she'd soon drive off the lot. You never see people this excited at Hertz.

The car I'd reserved, a 1966 Ford Country Squire station wagon, had the heart of a muscle car—a 390-cubic-inch V-8 engine—but the body of a school bus, with seating for eight, including a pair of inward facing seats in the back. And as furtively formidable school buses go, it was mighty photogenic, with stacked headlights, a solid-wood roof rack, rear windows covered in vintage decals of U.S. state maps, and a perfectly preserved brownish red "Emberglo" paint job.

Choosing a landscape for a car is like choosing a wine for a meal. The Country Squire—which, I discovered, handled with all the nimbleness of a riverboat—felt like a natural pairing for the Mississippi River valley south of the Twin Cities. The curves would be gentle, and the views sweeping: high bluffs on one side of the car, water on the other. My family and I would pick up Highway 61 in St. Paul, hopscotching between it and Wisconsin's fantastically scenic Great River Road, exploring the small waterfront towns along the way. We'd stop for the first night in Red Wing, Minn., and the next in Alma, Wis., 98 miles downriver. The car came with a 150-mile-a-day allowance, and a request that we not venture farther than 100 miles from Minneapolis, should anything happen. Adam Karon, the program manager, told me that fewer than 3% of his rentals have had issues, and most of those are simple—a balky roof or a dead battery. After a quick orientation of the Country Squire, Mr. Karon sent me off to with a winking warning, "It'll take you 45 minutes to get gas in that thing. Everyone who sees that car will want to talk to you about it."

He was right, and then some. I hadn't even left Morrie's parking lot when a customer arriving with his family to pick up a birthday present—a day in a (reproduction) Shelby Cobra—came sprinting over. "Oh my God, a Country Squire!" he said, "I learned to drive in one of these."

The 1966 Ford Country Squire wagon from Morrie's Heritage at Wisconsin's Maiden Rock. PHOTO: Ackerman + Gruber for The Wall Street Journal

After picking up my wife and son at the hotel, we set off. The Country Squire was a one-car parade. People on the highway would point, wave and snap pictures as we drove. After an hour of driving (and waving back), we stopped in Hager City, Wis., for a lunch of broasted chicken (prepared with a pressure fryer) and fried cheese curds. In the parking lot, another customer approached us, complimented the car, and spoke admiringly of the state of the paint, telling me about his work as a car detailer. Repeatedly, in talking about the car, people would give keyhole views into their lives. Outside the National Eagle Center in Wabasha, Minn., I chatted with a Korean War vet who we found snapping pictures of the car for Facebook. After a slice of strawberry lemonade pie at Stockholm Pie & General Store in Stockholm, Wis., we connected with a young girl and her parents who pointed to the rear-window decals to indicate all the places they'd been.

Not long after lunch, we pulled into a turnout on the Great River Road to get a good look at the 400-foot-high Maiden Rock Bluff. We were followed by a trio of cyclists, one of whom promptly tumbled from his bike. They were on a mission, he explained, to stop at every bar they passed in the small towns along the river; they seemed to be doing exceedingly well. While we talked, another of the cyclists snapped pictures of the car, and, grinning, said of me, "It's Clark Griswold and the family truckster!" referring to the bumbling dad played by Chevy Chase in "National Lampoon's Vacation" and his hulking station wagon. Definitely more fitting than "Moneybags," I thought.

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The wagon's retro charms were undeniable, whether they harked back to 1966 or to 1983, when the Griswolds made their way to Walley World. Our ability to enjoy those charms was partly a matter of luck: While its floor vents and open windows kept us plenty cool, if we'd set out a day earlier when temperatures were pushing 90 degrees, we might have cursed the car's lack of air conditioning. Likewise, the rains that pummeled the area the day after we returned our Squire would have made for riskier driving owing to the wagon's lack of traction control and sash-style seat belts—safety features we take for granted now. Still, with auspicious weather, and an AM radio that sounded remarkably good thanks to the car's concert hall sized interior, the Country Squire made a quite comfortable vessel for time travel.

Chef Shack in Bay City, Wis. PHOTO: Ackerman + Gruber for The Wall Street Journal

The throwback theme was reaffirmed that evening during dinner at Chef Shack, in Bay City, Wis., just across the river from Red Wing. It's the kind of ambitious but low-key restaurant travelers dream of stumbling across. Patrons sip champagne cocktails while sitting on Adirondack chairs in the garden, then duck inside for grilled trout and baked Alaska. When I told chef Carrie Summer about our adventure, she immediately saw how an old car suited our journey. "There's something special about rural destinations like this, where there's very little going on. You go back in time."

Even time travelers need to sleep sometime, and the venerable St. James Hotel in Red Wing ably fit our needs. Our room overlooked the river and the old train depot, where Amtrak's Empire Builder still stops twice daily.

The next morning I found Richard DeVoe, Zoe Malinchoc and their Fox Red Labrador retriever, Reveler, contemplating the Squire. "My grandparents had one of these," said Zoe. "My mom was one of eight kids, so it was pretty necessary." They invited me to drop by their shop, Fair Trade Books. There, Richard explained the store's operating ethos: They give all first-time visitors a free book, after soliciting their interests. I mentioned that we were exploring the river valley, and stopping that night in the town of Alma, just two streets wide, established by Swiss immigrants in the mid-19th century. They sent me off with a copy of Alton Brown's "Feasting on Asphalt: The River Run," in which Mr. Brown rides the length of the Mississippi on his motorcycle, and stops in Alma as well.

When we stopped in the town of Pepin, Wis., we parked next to the studio of Dougie Padilla, one of the godfathers of the Minneapolis art scene. His work has the primitivism and frenetic energy of Jean-Michel Basquiat's paintings, shot through with Mexican iconography. His storefront is more workspace than gallery, but Mr. Padilla welcomed us in (through October he'll be open the third Sunday of every month, with the caveat that he's "eccentric and unreliable"). There was the obligatory car conversation: Mr. Padilla drove cross-country in a '48 DeSoto, but that was the least of his stories. He was, in his telling, a Zelig of the counterculture. Tales of walking hand-in-hand with Ram Das, an ill-fated spell with a Chicano underground militia in New Mexico and a corporate gig creating designs for World Cup uniforms. He promised that at least half of what he told us was true. Had we been driving a Hyundai Elantra, I doubt we would have heard any of it.

The Country Squire in the Stockholm, Wis. PHOTO: Ackerman + Gruber for The Wall Street Journal

We walked a block down to the river where the Harbor View Cafe faces out onto the Mississippi River's widest navigable stretch, Lake Pepin. Beyond its fare—hearty portions of sophisticated comfort food—the restaurant is famous for its chalkboard menu over the bar, which was changed frequently over the course of the evening, with patrons watching it like a stock ticker. When we returned to our car, we found two chapbooks of Mr. Padilla's poetry tucked beneath a windshield wiper.

The last leg of the trip led to Alma, where we spent the night in a rental apartment overlooking the Big River Theater. The next morning, after a hike up the bluff to Buena Vista Park for sweeping river views, it was time to head back. When we parked behind Homemade Cafe in Pepin for breakfast, owner Patty Wirth dashed out from the kitchen, ladle in hand. "Aw geez, would you look at that?" she said, taking in our wood-paneled chariot. They don't make 'em like that any more. Well, come on in. I'm glad you stopped here."

THE LOWDOWN / Road Tripping through the Upper River Mississippi Valley

STAYING THERE: When the St James Hotel opened in 1875, Red Wing, Minn. was the wheat-trading center of the world, and badly in need of lodgings befitting its lofty status. The hotel, now owned by the Red Wing Shoe Company, retains much of its opulent character today (from $109 a night, st-james-hotel.com ). Blue Door Properties owns three lodging options in Alma, Wis., a sliver of a town sandwiched between high bluffs and the Mississippi River. Along with a traditional inn, and a cottage, they offer apartments above the town's Big River Theater (from $110 a night, bluedoorinnalma.com ).

EATING THERE: Just across the river from Red Wing in Bay City, Wis., you'll find weekends-only Chef Shack, where Carrie Summer and Lisa Carlson turn out refined dishes inspired by global travel (6379 Main St., chefshackbaycity.com ). The official state fruit of Wisconsin is pie, or at least that's the sense you'll get after a visit to the Stockholm Pie and General Store in the town of Stockholm. Visitors agonize over the list of choices (Bumbleberry? Coconut cream?) posted on the chalkboard before bringing generous wedges pie to gingham-clothed tables for devouring (N. 2030 Spring St., stockholmpieandgeneralstore.com ). Fluffy pancakes, skillets of expertly made hash and generously filled omelettes make the Homemade Cafe in Pepin, Wis., a favorite for locals and a lucky find for visitors passing through (809 3rd St., facebook.com/homemadecafeofpepinwi ).

EXPLORING THERE: Simply driving Wisconsin's Great River Road (wigrr.com) and Minnesota's Highway 61, with detours onto some of their smaller tributaries is pleasure enough. But occasionally, you'll want to get out and stretch your legs. The Upper Mississippi River Valley is a birdwatcher's paradise, and home to hundreds of bald eagles. Visit the National Eagle Center in Wabasha, Minn., which lets you get up close and personal with their resident bald and golden eagles, and learn about their habits and habitat (50 Pembroke Ave. S., nationaleaglecenter.org ). Get a view of the river's expanse by hiking (or driving) to Alma's Buena Vista Park, on a bluff 500 feet above the mighty Mississippi ( almawisconsin.com )

SHOPPING THERE: Browse the rugs and textiles at Cultural Cloth, which commissions and imports the handiwork of female artisans in developing countries. (W3560 State Hwy. 35, Maiden Rock, Wis., culturalcloth.com ) In Red Wing, grab a good read at Fair Trade Books, where Minnesota nice extends to bestowing a complimentary (used) book on all first-time visitors (320 Bush St., fairtradebooksrw.com ). In Pepin, Wis., Dougie Padilla, a stalwart of the Minneapolis art scene, brings some edginess to the area (101 Main St., Pepin, Wis., dougiepadilla.com ).

Old Faithfuls

We asked three vintage-car rental agencies to share their biggest sellers and the unsung favorites in their inventory

Morrie's Heritage, Golden Valley, Minn.

This eclectic fleet of 18 cars tilts toward the sporty and iconic—the kinds of cars that make appearances at weddings and big-number birthdays. morriesheritage.com

A Road Trip With Retro Charm—and a Car to Match; Want to upgrade your driving vacation? Rent a vintage car that suits the destination. To wheel around time-capsule towns in the midwest, writer Matthew Kronsberg sought out a 1960s woody wagon. Plus: Classic car rentals in Italy and the Cotswolds

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