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.
