Jumbo’s Win Win is a modern roadside diner located on Highway 128 in Philo, California, serving travelers moving between Anderson Valley wineries and the Mendocino coast. The setup is simple and fast: orders are placed at the counter, with seating split between a compact interior and a dog-friendly covered patio.
The menu is tight and deliberate, built around high-quality ingredients and regional sourcing. Signature items include smash burgers, fried chicken sandwiches, and sidewinder fries. Specials rotate regularly and often feature unexpected combinations, like soft serve finished with olive oil, honey, sea salt, and fennel pollen. Beer, wine, and casual twists—like a splash of pickle juice in your pint—round out the drinks list.
The atmosphere is unpretentious, with small-town energy and a pace that suits quick lunches or low-key dinners. Jumbo’s Win Win is open daily and draws both locals and road-trippers looking for a break from wine country tasting rooms or coastal highway drives.
Owned by Scott Baird, previously of San Francisco’s Trick Dog, the diner keeps its culinary ambitions focused and functional — efficient without losing character.
Jumbo's Win Win
