With the crisp autumn breeze picking up, Indian Island Winery marked one final outdoor hurrah on Saturday, Sept. 12, offering visitors a full spectrum of local flair: award-winning wines, vintage horsepower, local craftsmanship, and the squishy, barefoot ritual of grape stomping.
The winery grounds hummed with activity both inside and out as guests gathered for the annual Grape Stomp, paired this year with a bustling Vendor Show and the winery’s second annual Classic Car Roll-In.
Co-owner Angie Winter was the central hub for all the afternoon’s goings-on, juggling registration duties for the roll-in, checking in grape stomp & costume contest entrants, and coordinating the Winery’s inner workings. “Today really centers around the grape stomp, which is a tradition here eight years running,” Winter noted. “Blending that with the roll-in and vendor show provides a taste of everything for everyone.”
By 1:00 p.m., classic car owners, motorcycle enthusiasts, and tractor collectors began filling the winery lawn and patio area.
Among the early arrivals, a blaze orange Dodge Challenger commanded immediate attention, while a trio of vintage Plymouths evoked classic car show nostalgia. Tucked nearby, a 1970 Buick Skylark convertible with rich brown leather interior captured the era’s charm, complete with a carhop-style window tray holding classic A&W burgers and glass root beer mugs.
The undisputed standout of the display was a sleek, ruby-red 1927 Buick—affectionately known as the “Whiskey Six,” reminiscent of the Al Capone era. Its owner, Brian, who has owned the vehicle for several years, noted this was only its second public outing of 2026. The Buick delighted onlookers each time Brian sounded its authentic Ooga horn, sending a loud “awoooogah” echoing across the vineyard.
Inside the warm shelter of the winery’s dining hall, a dozen local businesses set up shop for a vibrant vendor fair. Prospective shoppers browsed a rich variety of handcrafted goods, boutique fashion, and gourmet treats.
Participating vendors included staple favorites such as Big Mood Boutique, Voges Bread and Bundt, Cotton Creations featuring hand-carved wooden candle bowls, Northstar Nouveau, Mary’s Angels, and Gray Duck Syrup Co. Tables overflowed with fresh artisanal breads, baked goods, hand-stitched towels, handcrafted jewelry, and cozy fall decor.
Soundtracking the festivities throughout the day was a continuous slate of live music, featuring morning-to-afternoon acoustic sets by Kris Karr on guitar and harmonica, followed by swing rhythms from the Real Big Band, and an evening finale by the Murphy Brothers.
While fine wine and hot rods drew steady crowds, the centerpiece of the day remained the competitive grape stomp—and the wildly creative costume contest that accompanied it.
Spectators cheered and voted on an array of colorful guises, including a duo dressed as Lucy and Ethel from I Love Lucy, a pair of Margaritaville enthusiasts complete with a parrot hat, and two women sporting spooky zombie makeup as the “Grape Reapers.” Taking top comedic honors was a married couple dressed as a medical team: the wife as a surgeon and her husband as a patient wearing a hospital gown, a head bandage, and a prominent pair of novelty plastic bare buttocks.
When the time came for the main event, 15 two-person teams—30 stompers in total—stepped into their designated plastic tubs for three minutes of high-intensity, barefoot squishing.
Before the countdown began, co-owner Ray Winter reviewed the ground rules with the contestants, offering one critical piece of advice: “Don’t lean on the support bars, or you’ll end up with a face full of dirt!”
At the signal, participants plunged into the tubs with furious intent. The squelch and pop of green grapes quickly turned into a fine paste, sparking fits of laughter from the crowd while some stompers grimaced at the cold, squishy sensation between their toes.
As the three-minute timer expired, teams carried their pulverized yield to a large strainer station, where judges carefully measured and recorded the volume of extracted juice to determine the winner. The superior stomper came from the tandem of Stacey and Tami with a yield of 1.210L.
Fresh out of the tubs, contestants rinsed their sticky feet in clean water, braving the cool afternoon wind with smiles and warm wine in hand—closing out another memorable season at Indian Island Winery.
