Weekend Wanderlust: Insights from the Epic 100-Mile Garage Sale Trek from Twin Cities to Winona

Heading south through downtown Hastings on Thursday morning, the initial "Yard Sale" indicator from Hwy. 61 led to a spot where you could get a bowling pin for just one dollar and an vintage sewing machine priced at $100.

It was the first day of the 100 Mile Garage Sale , taking place along both the Minnesota and Wisconsin banks of the Mississippi River, approximately from Hastings to Winona.

This massive shopping event, featuring over 200 sellers, has spanned more than twenty years since its inception during the '90s when it began as an 85-mile yard sale. Visitors travel all the way from states like Texas and Maine just for this occasion, often loading up their recreational vehicles with various goods. Regular attendees value not only the deals but also the sense of community fostered each year. They approach both pragmatically and whimsically—using savings from purchasing items such as pressure cookers to indulge in another attraction: a bake-off offering ten different types of homemade pies.

The farthest stall along Hwy. 61 was managed by Sheila Judge. According to her, hundreds of customers attended last year, with some arriving early to search for bargains as she and her companions were still arranging their setup. The attendees purchased extensively—ranging from unattractive ceramic vases to eerie dolls—that Judge began fetching additional items from inside the house. "Our stock depleted quickly," she mentioned.

The team had also achieved revenues totaling four digits. As Judge pointed out, the adage held water: "What one individual considers trash can be valuable loot for someone else."

Shortly after 8 a.m., Michelle Liberty found herself inside Judge’s "she shed," examining the collection of bar tools and cigar rollers. As a resident of Saint Paul, Liberty sees herself as somewhat of a garage sale ethnographer. She enjoys exploring other people's living spaces—such as Judge’s sofa, television, and pictures of Viking athletes—and speculating about their lifestyles. "I simply enjoy browsing through other folks' belongings," remarked Liberty. "It allows you to wonder, 'Who might these people be?'"

Liberty was looking forward to purchasing some patio furniture. Meanwhile, her sibling, Dave, traveled from St. Cloud with the intention of finding a blender. "Since this is my initial summer after retiring, it feels as though I have plenty of free time," he explained. His offspring, Brittany, who happens to be a mother, compiled an extensive shopping list for various necessities.

However, they might be enticed to deviate from the plan. For Liberty, this distraction came in the form of a charming set of pink-fringed toss cushions. "These have such a bohemian vibe; hence, I'm getting them," she stated.

Residents advise steering clear of the 100-mile stretch during weekends, as drivers frequently crane their necks and tap their brakes. At speeds nearing 60 mph, signage changes rapidly, ranging topics from "cheese curds" to "fishing equipment."

At Nicole Wuollet’s home in Red Wing, visitors would know they were near the sale by catching the aroma of doughnuts her mother was cooking next to a cooler filled with fresh rhubarb from the garden. Both sisters noted that several patrons come back each year because of their meticulously arranged collection of children's items at very reasonable prices. "Our main drawback," Wuollet sighed, "is that we rarely have time for browsing garage sales ourselves." She added jokingly, "Perhaps our spouses see this as an advantage."

The family had recently witnessed an unexpected repeat occurrence. The previous year, they assisted a woman who was frantically searching her yard sale for her misplaced engagement ring, thinking she might have dropped it somewhere along the way. "We looked all over for her but couldn't locate it," Wuollet mentioned. "This year, she returned and shared that she discovered the ring six months later inside her dresser."

Around noon, the rain began pouring down. In an auction hall on the opposite side of town, Kristi Flynn stood near her garage smoking a cigarette and playfully suggested setting out some umbrellas. ("They'd fly off the shelves.") Just a minute later, members from a multi-generational group arrived: two sisters planned to spend the upcoming three days shopping alongside their grown-up daughters for a girl’s getaway.

Each of them had on identical caps adorned with winged dragon brooches, symbolizing fantasy-romance book series Flynn inquired about the storyline, which led to a discussion about the playful yet contentious relationship between dragons and their riders.

During yard sales throughout Flynn’s neighborhood, shoes and suitcases became damp, yet the life jackets remained dry. A woman raised a tarp to inspect an assortment of free items and pulled out a toy for her child. "Free amusement," she remarked. This could also be called "yard sailing."

Here’s some financial guidance: Never purchase a brand-new puzzle since they’re abundant at garage sales. The same applies to croquet sets and panini presses. You can find secondhand China sets for nearly the cost of disposable plates. However, individuals attempt to make money off used milk cartons, worn bras, and empty medicine containers as well.

The 100-mile sale genuinely offers everything under the sun. You can find motorcycle jackets, formal prom dresses, and fragrant candles. It also includes items like a bonsai tree, a snowblower, and an ice auger. There are old yearbooks, a trumpet, and artificial decorative fruits available as well. The collection features Kenny Rogers vinyls, classic Barbie dolls from yesteryears, and Tonka toy trucks. Additionally, you'll discover hand-cranked drills and telephones. And yes, "Fargo" on VHS tapes is up for grabs too.

A 40-year-old garage sale enthusiast has made a name for himself by refurbishing and restoring vintage beer signs before decluttering his extensive collection stored in their basement. His spouse playfully remarked about how this hobby prevented him from frequenting bars. Additionally, they offered a trailer priced at $400 to transport one's discoveries.

Close to Lake City, Ed and Janet Plein from Kasson, Minnesota, have been operating their miniature doughnut truck at the same roadside location annually for twenty years. The only interruptions were due to cancellations caused by the pandemic and an unexpected blizzard. When the owners of the property where the Pleins set up shop sold it, they informed the new proprietors that using this spot came as part of purchasing the house.

Ed mentioned that he doesn't believe the size of the crowds fluctuates based on economic circumstances since buyers consistently enjoy finding great deals. "Garage sales usually attract individuals who are searching for those rare, once-in-a-lifetime finds akin to a Willy Wonka golden ticket," he explained.

Despite not purchasing anything over the course of the 100-mile journey—how!?—the scenic drive itself makes the excursion worthwhile. In this stretch, the Mississippi flows lazily, nearly resembling a vast lake as it winds between imposing cliffs. During this season, vivid green shoots emerge from the dull-gray twigs. Additionally, the eerie backwaters teem with skeletal trees and muddy waters.

The scenery along Wisconsin’s Highway 35 resembles its close relative, State Route 61. The garage sale items here share similarities but stand out due to an array of Green Bay Packers merchandise. One notable stop is the charming "Bread Hut," located right after crossing the Winona Bridge, north of Trempealeau, WI. This place offers sourdough loaves through an honesty-based payment system. Another interesting spot is in Alma, where the American Legion hall exudes a grandfather’s basement atmosphere and sells golf balls packed in egg cartons.

Between Pepin and Prescott, once you've passed your 29th croquet set and thought about strapping an oversized inflatable Corona bottle into your car, you'll realize it's time to stop garage sailing.

On Thursday, the last bit of frustration came from seeing two throw pillows identical to those Michelle Liberty had bought just eight hours prior during her initial sale. However, these were priced a dollar lower at the current sale.

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