Love & Squalor Wine is turning 20 this year, and the Southeast Portland winery is marking the milestone with something messier than a toast: a grape-stomping showdown pitting twenty teams against each other to see who can crush the most juice by foot in five minutes flat. The event lands on October 10 at the winery's South Tabor crushpad, complete with an “I Love Lucy” look-alike contest, wine, food, and music.
The competition was announced by KATU, which spoke with Matt Berson, the winemaker and co-owner of Love & Squalor, and Angie Reat, the label's co-owner and general manager, about the upcoming celebration. Tickets are still available for the October 10 event, according to the station's report. Twenty teams will compete to stomp the most grape juice during a five-minute sprint, with the winery layering in food, music and wine to round out the party atmosphere.
A Thrift-Store Novel Sparked the Brand
Berson launched Love & Squalor back in 2006 with a modest first run of just 65 cases, naming the label after a thrift store copy of J.D. Salinger's *Nine Stories* he stumbled across, according to Prince of Pinot. Before settling into a permanent home, Berson made his wines for years in a shared winery in McMinnville. The brand eventually found its base at Portland Wine Company's facility at 3201 SE 50th Ave, a 5,000-square-foot urban winery and tasting room that opened in October 2019 and now houses Love & Squalor alongside several sibling projects, per the Oregon Wine Board.
That same Southeast Portland facility ferments and bottles more than just the flagship label. According to the Willamette Valley Wineries Association, the site also produces Garageland, Pet Matt sparkling wines, the Mothershucker white blend, and the Marty red blend, all crafted and bottled on site.
Where Grapes Meet the City
The crushpad sits in the South Tabor neighborhood, immediately south of Mount Tabor Park, which is a 176-acre city park built around an extinct volcanic cinder cone, according to Lovejoy Real Estate. South Tabor extends from Division Street down to Powell. Portland is home to more than 30 wineries, and the PDX Urban Wineries Association lists 16 members.
That model lets residents watch commercial winemaking happen without a drive out to the Willamette Valley. The October 10 event also falls squarely within Oregon's harvest and crush season, which typically runs from September through late October as wineries process incoming fruit in real time, according to the Willamette Valley Wineries Association.
A Down Harvest Year, Still a Big Industry
The stomp arrives amid a notably smaller Oregon harvest than in recent years. The 2025 Oregon Vineyard and Winery Census Report, published in July, found that Oregon wineries crushed 73,771 tons of wine grapes statewide — a 23% drop from 2024 — while Pinot Noir remained the dominant variety, making up 59% of planted acreage, according to the Oregon Wine Board. Even so, the industry's overall footprint remains massive: the Oregon Wine Board's 2024 Economic Impact Report, released in February, found the state's wine and wine grape industry generated $8.49 billion in economic impact and supported more than 38,000 jobs.
The event includes a costume contest. The CBS sitcom episode “Lucy's Italian Movie,” which aired April 16, 1956, featured Lucille Ball in a slapstick grape-vat brawl with actress Teresa Tirelli, according to Vintage Everyday. Ball's scene remains one of classic television's most enduring comedy bits.
Not the Only Grape Stomp in Town
Southeast Portland isn't unfamiliar with grape stomping as a community draw. The neighborhood's Italian Festival of Portland featured its own grape stomping and bocce games at St. Philip Neri Catholic Church on SE 16th Avenue in August, suggesting the activity has become something of a recurring fixture for local harvest and cultural celebrations. With tickets still available, Love & Squalor's 20th-anniversary stomp gives Southeast Portland another shot at getting its feet purple before the season winds down.
