Tucked away in the rolling hills of western Mendocino County on California’s State Route 128 (SR 128) is a tiny, laid back town that is known for its wineries and access to various outdoor activities.

If you want to do some wine tasting in a forest-setting surrounded by tight-knit community vibes, then look no further than Philo, California.

Philo is a town that has a nice blend of agriculture and art; Golden Eye Winery and Husch Vineyards are a couple examples of the many wineries in town that offer tastings with scenic beauty that inspire the local art scene due to the nature scenery.

But with the wine and art scene grabbing all of the attention in Philo (and rightfully so), there is a new burger spot situated on the westbound side of SR 128 that has been building up its own reputation.

Started in 2024, Jumbo’s Win-Win hopes to serve burgers to their community for years to come as all of their product are local and organic.

Whether it’s a Jumbo’s Burger, Fried Chicken Sandwich, or soft serve ice cream, they offer an affordable menu that is guaranteed to have the best quality.

This roadside burger stand is owned by Scott Baird, who co-founded the Trick Dog cocktail bar in San Francisco as well as Donna’s Pickle Beer (you heard that right).

A Bay Area native with an impressive resume (i.e. chef, bar owner, and beverage consultant), Baird moved his family up to the Anderson Valley for a more quiet setting.

And in the short amount of time that Jumbo’s has been open, it has already established into a local staple for the community of Philo and is also frequented by visitors or people just passing through.

My wife and I recently spent a vacation celebrating our 1-year wedding anniversary in Fort Bragg, which is approximately an hour drive west of Philo taking the route where SR 128 meets California State Route 1 (SR 1).

I knew about this spot for about a year now after reading SFGate travel editor Silas Valentino’s October 9, 2024 article raving how good Jumbo’s is, and made this the first stop during our journey.

Jumbo’s is open daily from 11AM to 8PM, and we arrived about a half hour after opening. I immediately noticed how the restaurant had that classic, nostalgic feel to it on the inside.

My wife and I love a good smash burger, so we both went with a double Okie Onion Smash Burger ($13 each, $9 for a single patty). The burgers featured organic 3M cattle beef, cheese, grilled sweet onions, pickles, and their special sauce.

Fries are ordered separately, and you have the option of either the sidewinder version ($5) or Jaspers (named after Baird’s eldest son) hand-cut fries ($7). We went with the Jaspers.

You can either sit inside the restaurant or outside in the back where you can look at the beautiful, Anderson Valley Hills which is what we did.

The smash burgers were juicy and had great flavor, complimented by the crisp pickles and onions along with what seemed like a beer sauce. Their fresh buns are nicely toasted

The Jasper fries were amazing, but what is more amazing is the long, two-day process it takes to prepare them. The fries are soaked in water overnight then boiled before being removed to cool down.

This process ensures a crispy exterior to the fries and fluffy potato on the inside. You can also taste the authenticity of the freshness.

I have been anxious to try Jumbo’s since they appeared on my radar, and I was not disappointed at all.

But I have to go back to that pickle beer I mentioned earlier.

Donna’s Pickle Beer is sold at Jumbo’s for $5 a can, but can also be purchased online.

The Alcohol by Volume (ABV) level in a Donna’s is about 4.4%, and it is an American lager infused with pickle brine.

There is a legend on how this all came about labeled on the side of the can.

It’s definitely an interesting combination, to say the least; and it’s definitely not for everyone. Bottom line – you either like it or you don’t.

But I am all for trying something at least once, so I had to document my experience.

Overall, I did get hints of both lager and pickle flavor. It wasn’t bad really, and the pair together really work if you’re feeling adventurous.

I’m more into bolder beers such as IPAs or red ales, so I don’t know if the pickle brine would work with those types of brews. But the Donna’s I would try again without hesitation.

After getting our fill of burgers and fries (and the pickle beer in my case), we thanked the wonderful staff for their hospitality and continued on our journey to Fort Bragg.

This burger joint is a must-try if you’re ever traveling along SR 128 through Philo. I plan on going to the Mendocino Coast more often, and Jumbo’s Win-Win will always be a stop along the drive.