Jumbo’s Win Win was a roadside burger spot that opened in August 2024. Scott Baird, a James Beard nominated bartender and his wife Molly moved to the Anderson Valley in 2020, escaping the hectic living of San Francisco. They wanted to offer a limited but well composed menu and interestingly chose the building which is a 120-year old former saloon. The name Jumbo is for the owner’s son, named by his brother who also suggested the name Jumbo’s Win Win. The fairly large spot had a long counter where you placed and picked up your order. Next to that space a large window opened into the kitchen where the food was passed through and your name called out with a microphone. Tables and chairs filled the rest of the room and there was an outside patio if you wanted. Multiple windows added to the already bright room with just a few decorations. Actually, the bathroom had more visuals with custom-made tiles. Music was in the background and the counter person was very helpful. They are open every day from 11-8 in the Anderson Valley. It’s a cute family-run place that serves an okay burger and tasty dessert options. Stop by when you’re on CA Hwy 128 and need to fortify before visiting another winery.
Set-up
Food
The Okie Onion Smash Burger can be ordered as a single or double. The patties are 3 oz and I tried the double. It is made with organic 3M Cattle Co. beef, cheese, sweet onion, pickles and special sauce. The special sauce is mustard based and with a double patty you get double cheese. They got a good sear on the edge of the smashed beef patties but I would have like more onion.
We got the Jaspers hand cut fries which are a limited option but are triple cooked and not an ordinary frozen fries. They were a large cut with a fairly crisp exterior but the inside is where it excelled with fluffy potato interior. We each got an order which was too much – you could split one order for 2.
They had no seasonal flavored hand pie but did have the apple pie. They are cooked to order and have a delicious crisp, flaky crust witht a well-seasoned cooked apple interior. Don’t miss this one – it was great.
We wanted a cup of vanilla soft serve to go with the pie, which was a good plan but next visit I’m getting it with the honey and fennel and olive oil topping. They offer chocolate and swirl options, plain at $5 and toppings are extra. Alone it was fine but nothing special.
It’s interesting and good to see OK-style onion-smashed burgers become more popular. There are at least a couple places in my area that now serve them.
Thanks for your comment! I still am a fan of a nicely done one whereas my husband is gravitating back to thicker patties. Funny how we move the dial but it’s too hard to find with all the fast food places’ competition. I’ll have to get the names if and when we get back to the Philly area.
Right. Aside from the couple of onion-burgers I’ve noticed, a much bigger trend has been the move from thick pub-style burgers to double smash burgers in the Philly area.