Lessons from this weekend’s 100 Mile Garage Sale, from the Twin Cities to Winona

Driving south through downtown Hastings on Thursday morning, the first “Garage Sale” sign off Hwy. 61 pointed to a place selling a bowling pin for a buck and an antique sewing machine for $100.

It was opening day of the 100 Mile Garage Sale, held along the Minnesota and Wisconsin sides of the Mississippi River, roughly between Hastings and Winona.

The region’s biggest bargain-hunting weekend, with 200-some vendors, has been going on for more than two decades, expanding on the original 85-mile garage sale of the 1990s. Shoppers come from as far away as Texas and Maine and have filled RVs with wares. For some repeat customers, the annual sale is as much about camaraderie as deal-hunting. And being practical as well as charmed. Money saved on an instant pot can be later spent at a sale offering 10 kinds of homemade pie.

The northernmost sale off Hwy. 61 was hosted by Sheila Judge. Last year, several hundred shoppers showed up, Judge said, including early birds pecking for deals while she and her friends were still setting up. Shoppers bought so much — even the ugly clay pots and creepy doll — that Judge started pulling more stuff out of the house. “We ran out of inventory,” she said.

The group had also cracked four digits in revenue. The old saw, Judge said, was true: “One person’s junk is another person’s treasure.”

At just past 8 a.m., Michelle Liberty was in Judge’s “she shed,” perusing the barware and cigarette-rollers. The St. Paul resident considers herself something of a garage-sale anthropologist. She likes peeking into others’ homes — she pointed out Judge’s couch, TV, photos of Vikings players — and imagining their lives. “I just like looking at other people’s junk,” Liberty said. “And you can kind of be like, ‘What kind of people are they?’”

Liberty was hoping to buy patio furniture. Her brother, Dave, had come from St. Cloud seeking a blender. “This is my first summer of being retired, so it’s like: I got all the time,” he said. Dave’s daughter, Brittany, has kids, so she had a whole list of items.

Locals know to avoid the 100-mile route over the weekend, when drivers’ necks are craning and brake lights are flashing. The sale signs come up fast at 60 miles per hour, from “cheese curds” to “fishing gear only.”

At Nicole Wuollet’s place in Red Wing, shoppers could find the sale by the scent of doughnuts her mom was frying up beside a cooler full of garden rhubarb. Wuollet and her sister said some customers return every year due to their well organized, affordably priced stash of kids gear. “The biggest downfall is that we don’t get to do much garage sale shopping,” Wuollet lamented. “Maybe our husbands think that’s a benefit.”

The family had just seen a surprising repeater. Last year, they helped a woman scour their sale for her missing engagement ring, which she believed she’d lost somewhere along the route. “We searched everywhere for her and we couldn’t find it,” Wuollet said. “She came back this year and said she found it six months later in her dresser.”

By midmorning, it started raining. At a sale across town, Kristi Flynn smoked a cigarette beside her garage and joked about putting out a few umbrellas. (“They’d sell like hot cakes.”) A minute later, part of a multigenerational entourage pulled up: Two sisters were spending the next three days shopping with their adult daughters, as part of a girls’ weekend.

They all wore matching hats with winged dragon pins, representing a fantasy-romance book series they’d read. Flynn asked about the plot, starting a conversation about flirtatious, warring dragon riders.

Here’s some financial advice: Don’t ever buy a new puzzle, because garage sales are awash in them. Same goes for croquet sets and panini makers. Secondhand china sets sell for practically the price of paper plates. But also, people try to wring money from used milk cartons, worn bras and empty pill bottles.

The 100-mile sale truly has it all. Motorcycle jackets, prom dresses and scented candles. A bonsai tree, snowblower and ice auger. Old yearbooks, a trumpet and fake decorative fruit. Kenny Rogers records, vintage Barbie dolls and Tonka trucks. Hand-crank drills and telephones. “Fargo” on VHS.

One 40-year garage seller is known for cleaning up and repairing old beer signs, then offloading the excess from his vast basement collection. “It kept him from going to the bar,” his wife joked of the hobby. They were also selling a trailer to haul one’s finds for $400.

Near Lake City, Ed and Janet Plein of Kasson Minn., have brought their mini-doughnut truck to the same frontage road every year for two decades, except for the times the sale was canceled for COVID and walloped by a freak snowstorm. When the property the Pleins park in front of changed hands, they told the buyers they came with the house.

Ed said he didn’t think the size of the crowds changes in relation to economic conditions, as shoppers always delight in a score. “Garage sales are typically people out looking for the Willy Wonka golden-ticket-type thing,” he said.

The view from Wisconsin’s Hwy. 35 feels like the fraternal twin of 61. The garage sales on this side aren’t notably different, except for the abundance of Green Bay Packers apparel. Among the stops worth a mention are the adorable “Bread Hut,” filled with sourdough loaves sold on the honor system, just across the Winona Bridge, north of Trempealeau, Wis. And, in Alma, the American Legion hall has a grandpa’s basement vibe and sells golf balls by the egg carton.

Somewhere between Pepin and Prescott, after you’ve seen your 29th croquet set and considered buckling a human-size, blow-up Corona bottle into your passenger seat, you’ll know it’s time to quit garage sailing.