On Sunday, October 25, 88 Vines Entertainment is bringing its Vines, Views and Vibes series to Healdsburg. 88 Vines produces benefit events that put winemakers, chefs and musicians in one room, and the earlier editions of this one were held on a hotel rooftop in Napa. This one is on Roof 106, the open-air lounge above The Matheson, Dustin Valette’s restaurant on the Healdsburg Plaza, where the view carries out over the town and the hills behind it.

Liam Mayclem is hosting the afternoon. He is the food and culture reporter known as the Foodie Chap, whose interviews with chefs and winemakers have run on KCBS radio in San Francisco for years, and he carries the room from the pours through the music to the auction.

Valette Wines is pouring new limited releases made alongside other winemakers, so these are bottles that have not reached a shelf or a wine list yet. The Matheson kitchen cooks through the afternoon with what is in season at the end of harvest, and each plate is matched to a wine.

Experience a rare, intimate performance by rising soul-pop singer Izzy Escobar - hailed by Forbes as “Your Pop Queen for 2026” - following playing to tens of thousands at festivals including BottleRock and the Montreal International Jazz festival.

The afternoon raises money for the V Foundation for Cancer Research, which ESPN and the basketball coach Jim Valvano started in 1993 and which has since put more than five hundred million dollars into cancer research at treatment and research centers across the United States and Canada. Everything the silent auction raises goes to the Foundation, and the lots include wine, travel, music, sports and culinary experiences. Bottles of Valette Wines are also for sale on the rooftop, and twenty percent of those sales goes to the Foundation.

Doors open at a quarter to twelve and the afternoon runs from noon until three o’clock at Roof 106, 106 Matheson Street, Healdsburg. Guests must be twenty-one or older.