You simply cannot drive on highway 128 through Philo in the Anderson Valley and miss this place — in more ways than one.

First, with its huge block letter sign painted atop its building, Jumbo’s Win Win definitely sticks out.

Second, this retro, playful, family-run burger stand serves up classic burgers, sandwiches, fries, and soft serve with premium ingredients and top-notch techniques at shockingly affordable prices.

The New York Times even named it one of the best new restaurants of 2025. If you’re in the area, it’s an absolute must-stop.

It was opened last year by Scott Baird, the lauded James Beard-nominated cocktail and beverage consultant who co-founded the innovative Trick Dog bar in San Francisco.

Housed in a 120-year-old roadside building that was formerly a saloon, Jumbo’s is named after his youngest son.

The operation is a true family affair, with his wife, Molley Green, responsible for the whimsical diner-like design, complete with red accents, a plaid floor, and wooden deer and bear heads on the walls.

The outdoor dining area is a kid’s delight with tortoise and rhino stone sculptures, as well as a fake life-size horse.

Order at the counter, then wait for your food to be ready to pick up.

The Jumbo’s single-patty burger ($10) of organic 3M beef comes snuggled inside a soft toasted bun with cheese, onion, iceberg lettuce, pickles, and a creamy, mustard-laced sauce. Good thing we were there in late-summer because Jumbo’s only adds a tomato slice to burgers during tomato season.

The coarsely ground burger fairly bursts with juiciness from the first bite. In fact, it pays to eat this burger in a timely manner as the longer you take, the more the bun will begin to disintegrate. So, don’t dawdle. Don’t engage in long conversation with your dining companion. Just eat.

The fried fish sandwich ($13), which often sells out, is made with local rock cod. It is what you wish a filet-o-fish could be. Flaky and moist, this is fish that really tastes fresh. Nicely crisp all over, it’s topped with a creamy cabbage slaw and dill tartar sauce.

Two types of fries are offered: twisted sidewinder ones ($5) perfect for scooping up a lot of ketchup; and Jasper’s hand-cut ones ($7) that are named for Baird’s older son. We went with the latter, and they are a marvel.

They require quite the process, too: soaking overnight, then simmering, draining and cooling before being fried. It’s a method apparently perfected by Michelin three-starred chef Heston Blumenthal.

All that meticulousness adds up to some of the best fries I’ve ever had. They are completely crispy all over. They’re thin, but not too thin, which is a good thing because there’s ample flesh inside to savor for its unabashed creaminess. Interspersed among the whole fries are little bits and bobs, which you should not let go to waste, because they are some of the crunchiest parts to enjoy.

The seasonal hand pie ($5) arrives burnished, flaky, crispy, and almost too hot to handle right out of the fryer. I only wish there had been more pear filling, as after one bite, I peeked inside of the pie to find only a mere smidge of jammy fruit with a mostly hollow interior.

Thankfully, I still had a few more of those fabulous fries to end on instead.

More: Gourmet Getaway to the Mendocino Region, Part I: Michelin Two-Starred Harbor House

And: Gourmet Getaway to the Mendocino Region, Part II: The Historic MacCallum House

And: Gourmet Getaway to the Mendocino Region, Part IV: Boonville Hotel and Offspring Restaurant