20 Teams, 5 Minutes, And A Thrift Store Dream: How One Southeast Portland Winery Crushed The Competition To Celebrate Two Decades

In the sprawling tapestry of the American West, cities often encroach upon the land, yet they occasionally choose to embrace it rather than conquer it. This philosophy anchors the spirit of what is happening in Southeast Portland this October. Love & Squalor Wine is turning 20 this year, and the Southeast Portland winery is marking the milestone with a visceral celebration of its roots. The event is 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 competition lands on October 10 at the winery's South Tabor crushpad, an urban setting that transforms the quiet industrial neighborhood into a scene of festive chaos. This gathering is not merely a party; it is a testament to the way the agricultural spirit survives and thrives within the concrete jungle. The atmosphere is complete with an "I Love Lucy" look-alike contest, wine, food, and music, creating a carnival-like environment that honors the messy, physical labor of the harvest season. As officials note, the station's report suggests the day will offer much more than just the spectacle of crushed grapes.

The history of Love & Squalor is a fascinating chapter in the modern West, one that begins not in a pristine vineyard but in a second-hand shop. Berson launched Love & Squalor back in 2006 with a modest first run of just 65 cases. The brand was named after a thrift store copy of J.D. Salinger's *Nine Stories* he stumbled across, a literary nod that adds a layer of intellectual depth to the brand's identity. This origin story highlights how the West is built on story as much as soil. Before settling into a permanent home, Berson made his wines for years in a shared winery in McMinnville, a journey that reflects the itinerant nature of early American winemaking. 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. This facility now houses Love & Squalor alongside several sibling projects, proving that the urban winery model allows commercial winemaking to exist seamlessly within residential areas. Per the Oregon Wine Board, the site also produces Garageland, Pet Matt sparkling wines, the Mothershucker white blend, and the Marty red blend. This diverse production capability indicates that the facility is a true engine of the local economy, fermenting and bottling more than just the flagship label.

The location itself, South Tabor, offers a unique geological and cultural vantage point. 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. This urban oasis provides a stunning backdrop for the harvest festivities, connecting the agricultural act of crushing grapes to the ancient geological forces of the region. South Tabor extends from Division Street down to Powell, placing the action right in the heart of a vibrant urban district. Portland is home to more than 30 wineries, and the PDX Urban Wineries Association lists 16 members. This model lets residents watch commercial winemaking happen without a drive out to the Willamette Valley, democratizing access to the industry. 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, this timing allows the public to witness the industry's pulse.