Jumbo's Win Win - Online Orders Available! — Restaurant in Ukiah

What happens when a SF bar legend opens a modern Americana diner in the heart of Anderson Valley? Pure magic, that's what. Jumbo's Win Win, helmed by Scott Baird (co-owner of SF's acclaimed Trick Dog), has become my family's mandatory pit stop between wine country and the Mendocino coast. So mandatory that we ate here THREE times in one weekend during our mushroom foraging adventure!

The setup is refreshingly simple - order at the counter, then prepare for some of the best casual eats you'll find in Northern California. The menu is focused and intentional, spotlighting local purveyors and organic ingredients whenever possible. Let me break down the must-orders:

The burgers? Perfection. The fries? INSANE (seriously, don't you dare skip them). But the sleeper hit is their mind-bending soft serve topped with honey, olive oil, sea salt, and fennel pollen - a combination that sounds wild but works brilliantly.

We've basically eaten our way through the entire menu at this point - stellar chicken sandwich, fantastic fish sandwich, and surprisingly crave-worthy salads. The rotating specials keep things interesting, and the drink selection is on point (would you expect anything less from a Trick Dog alum?).

What really seals the deal is the vibe - it's that perfect blend of local hangout and traveler's oasis. You'll see regulars catching up at the counter while road-trippers like us plan their routes specifically around hitting Jumbo's for lunch.

Pro tip: If you're heading up to Mendocino or exploring Anderson Valley, this is your spot. The quality and execution put most big-city spots to shame. Just don't blame me when you find yourself making excuses to drive through Philo just to grab another burger.

One last time for those in the back: DON'T. SKIP. THE....

I predict this place will become a worldwide destination. If you are ever touring Mendocino County wine country you have to stop here for a burger. Every ingredient is the best available and that's why the food tastes so good. The meat is local, they use the best potato buns, tomatoes, lettuce, cheese - even the ketchup is Heinz Organic (America's Test Kitchen's top-rated). The sidewinder fries are outstanding. The sweet onions on the smash burgers are incredible. Someone still makes it they way they used to!

It's out of the way in little Philo, CA but it's a beautiful drive through lush wineries you'd never see otherwise. Napa and Sonoma wine country is fantastic, but Mendocino wine is inexplicitly under-appreciated. It's really fantastic world class wine and the tastings out here are cheap and generous.

Jumbo's Win Win is just stellar. Imagine if In-N-Out burger used only the finest ingredients in every possible category and that's what the burgers are like at Jumbo's. Easy to drive by this place -- but don't. They are open every day and usually busy, but service is fast. Nice indoor and outdoor seating and dog friendly. Soft serve ice cream, slushies, local craft beer on tap -- they thought of everything you'd want. The ultimate hamburger stand from days gone by still exists...

Jumbo’s in Philo is a full-blown roadside miracle disguised as humble burger shack. It doesn’t scream for attention, but it absolutely deserves it. This place serves up the kind of burger that makes you roll your eyes in pleasure and question why you ever settled for fast food mediocrity. The patties are juicy, seasoned just right, and stacked like they mean business with fresh condiments, melty cheese, and buns that don’t fall apart mid-bite (because we’re adults here, barely).

The fries are golden perfection, best I’ve had in a very long time. They also have gargantuan hot dogs, chicken sandwiches and more. Jumbo’s is the real deal: no pretentious menu, no overthought branding just unapologetically good food served up with small-town realness. Sit your happy butt down at a picnic table, breathe in that Philo country air, and devour something that actually satisfies.

It’s the kind of spot you brag about discovering but secretly hope never gets too popular. Because Jumbo’s isn’t just a burger stop it’s a glorious rite of passage. You came for the food, but you’ll come back for the feeling. And maybe a...