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    Jumbo's Win Win

    4.8 (149 reviews)
    Closed 11:00 am - 8:00 pm

    Jumbo's Win Win Photos

    Jumbo's Win Win - Soft serve ice cream - Burgers Near Me - Philo, California
    Jumbo's Win Win - El Ruben birria pastrami sandwich with hand cut fries 12/10 - Burgers Near Me - Philo, California
    Jumbo's Win Win - Burgers Near Me - Philo, California
    Jumbo's Win Win - Jumbos burger - Burgers Near Me - Philo, California
    Jumbo's Win Win - Soft serve - Burgers Near Me - Philo, California
    Jumbo's Win Win - Veggies abound and those sidewinders! - Burgers Near Me - Philo, California
    Jumbo's Win Win - Burgers Near Me - Philo, California
    Jumbo's Win Win - Cheese burger and fries - Burgers Near Me - Philo, California
    Jumbo's Win Win - Mushroom quesadillas - Burgers Near Me - Philo, California
    Jumbo's Win Win - Burgers with sidewinder fries. - Burgers Near Me - Philo, California
    Jumbo's Win Win - Burgers Near Me - Philo, California
    Jumbo's Win Win - Burgers Near Me - Philo, California
    Jumbo's Win Win - Chicken Sandwich - Burgers Near Me - Philo, California

    +221

    Jumbo's Win Win - Minimalist interior - Burgers Near Me - Philo, California

    JUMBO'S WIN WIN ATMOSPHERE

    What's the vibe?
    Moderate noise
    Good for kids
    Dogs allowed
    Outdoor seating

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    Jumbos burger
    Crystal C.

    Made a stop up here on the way to the Mendocino coast and while wine tasting at the many vineyards on the road. Ordered the Jumbo's burger (single) and the pickle dog. The burger was pretty straight forward. Ordered it spicy and it was indeed spicy!! Felt like the iceberg in this somewhat watered down the richness of the meat and I might elect to get a double or the Okie Onion smash burger should I make my way back. The hotdog had a bunch of pickle jalapeño relish which made it quite wet and cold. Was also missing the characteristic snap of a good sausage. Otherwise appreciated the brightness of pickle and mustard. Both items came out lukewarm. I might not specifically make my way out to come here but works well if you're passing through.

    Burger and fish sandwich with fries
    Es F.

    Loved the counter service, the enormous patio and casual atmosphere. It's the kind of place that you end up talking to people at the next table. Don't rush a visit here. Try the burger and chicken sando and we thought the regular fries were delicious!

    Double Okie Onion Smash Burger
    Rick M.

    Finally... finally... FINALLY stopped at Jumbo's Win Win in Philo. Headed back to Bay Area early after a stay on the North Coast, and the magic formula for not wading through the ever present lines and crowds at this roadside institution seemed to be a midweek lunch stop. Maybe 6 people total already there. Walked in and gave the menu a quick look over. There's the regular menu plus a few specials listed to the side. Wine, beer, and soft drinks available on a menu near the register. It was a toss up between the Jumbo Burger or the Okie Onion Smash Burger. After some advice from the friendly counter person, I went with the Okie Onion Smash Burger, double patties. Husband ordered the Chicken Karaage special. Bottled sparkling water and a Pliny the Elder brought us in at $42 tab (plus tip). We grabbed seats in the garden out back with was super pleasant with lots of tables, chairs, and fun artwork. You could even ride a hippo or a giant tortoise while eating if you're so inclined. Food was brought out to us (normally they call numbers, but it was on the quiet side today). My Okie Onion Smash Burger was huge. Grilled onions, melty cheese, double patties, and generous portions of crisp iceberg lettuce, pickle, and tomato slices topped the meat, and the toasted brioche bun was slathered with a thousand island-like spread. I was able to use my hands for about half, but had to resort to a knife and fork to finish it off. A delicious mess! Husband liked the chicken karaage, but they were more chicken nuggets than karaage. When I think of karaage I think shatteringly crisp pieces of chicken in a light potato starch breading. This was more cornmeal breaded and fried. Good, but not quite karaage. No complaints tho as it was also delicious with the spicy mustard. Didn't order fries or ice cream this trip, but that's what the next trip to Philo is for. What's left to say? Great food. Great drinks. Come off peak hours for an easy in and out experience. Def a must stop!

    Onion smashburger and fries
    Caly T.

    Such a great pitstop for food along the highway! Friendly service and plentiful indoor and outdoor seating. - Onion smashburger: loved the potato bun and the burger was properly sauced up. The onions and pickles were delish in this! - schwinger fries: perfect combo of fluffy and crispy!!! Loved these - soft serve: creamy but also light, such good flavors in the greek toppings - the fennel was delightful!

    Single burger
    Kathleen L.

    We stumbled across Jumbo's during our drive back from Mendocino. We drove past it, but saw some people go in and we turned around and decided to get some food. The exterior and interior of this shop is super cute! Love the diner feel of this spot. The line to order was short and we thought ok, it shouldn't be too bad of a wait because the line to order was short and it's burgers and fries, so it shouldn't take too long. We ordered one Jumbo's burger (single), sidewinder fries and pickle beer. We didn't want to order too much since we were just driving back home and wanted a little "snack." We ordered at 1:53 pm and didn't get our order until 2:50 pm!! During that wait, we were getting very impatient. We got our food and ok.... We were blown away. My boyfriend and I were just so annoyed and we were just like, this better be worth the wait and well...it was worth the wait. So, knocked down one star, other than the wait, would've been a five star spot for us. Can't wait to come back to this spot!

    Steve W.

    This looks like your typical roadside diner but it's on another level. The burgers are first rate and could be found on top ten lists. Its slick interior, hospitality, and fun atmosphere are a plus. I had an excellent smashburger with cheese, grilled onions, pickles and just the right amount of edge crispiness. The fries are excellent. They have a nice variety of beers, wines, plus an irresistible soft serve ice cream. Don't pass this one by!

    Davis Y.

    A MUST stop, burger (and more) diner on the 128! Smash burgers were cooked perfectly and the hand cut fries were some of the best fries I've ever had. Topped it off with a soft serve ice cream in the back patio area. Will be making this a stop every time I'm on the 128

    Jumbo singles
    Cecelia P.

    Excellent food. The hot dog with pickled mustard seeds was very good. Cheeseburger was delicious and for dessert I recommend the Greek ice cream cup. First time I ever tried olive oil and flaky salt on my soft serve. I recommend eating there.

    Okie Smashburgers with Jasper Fries
    Paul W.

    Stopped here along the way to Fort Bragg for a quick stop and bite to eat. I heard this place had great smashburgers despite being in a remote area on Hwy 128. But news spreads fast and here I am. We both enjoyed the okie smashburger and Jasper fries. The burgers were juicy and had lots of flavor. The grilled onions and pickles were a nice touch. The fries were great too. Crispy and I could tell by the taste they were fresh organic. The pickle beer was a first for me... and the other reason why I wanted to check out this spot. It's interesting. You get hints of both pickle and beer at the same time. It wasn't that bad actually. Overall this place is a hidden gem. You can eat inside or outside and enjoy the beautiful scenery of the Alexander Valley. The outside seating area is pretty nice. I wish I would've got the name of the cashier because she was very friendly and helpful. Makes everyone feel right at home. I would definitely make this my go-to stop whenever I'm headed to Mendocino County.

    Soft serve 5$
    Vineesha D.

    Stopped here for a quick bite on the way to Mendocino. Cool little spot with nice interior, self-service setup, and some outdoor tables too. We tried the chicken sandwich, pickled beer, fries, and soft serve, one plain and one with fruit. Just FYI, the sandwich doesn't come with fries, it's $14 by itself, fries are $5, beer $5, and soft serve $5 (extra if you add fruit). The chicken sandwich is hands down the star, super juicy, crispy, piping hot, with a toasted bun and finger-licking sauce. Worth trying at least once, though $14 feels a little steep. Fries were solid, some a bit on the thicker side but still good. The soft serve was a miss for us, not great flavor, and the fruit topping was more like a jam, which was kind of off-putting. The beer is very interesting and my family liked it very much. Overall: stop in if you want a quick snack and definitely go for the sandwich. Just skip the soft serve.

    Ajay K.

    This was the perfect stop on a long roadtrip: I can't believe how fresh everything was given that they're kind of in the middle of nowhere. The Greek style soft serve was my absolute favorite and they make a mean smash burger too. I had also never seen fries in this shape and I can understand why they are so popular now! Look forward to trying more on my next trip.

    Very good brewed root beer.
    Adrienne A.

    This is a very nice place to stop and have lunch. It's very clean and they have nice music playing. The service was great, you order at the counter. They have outdoor seating, and I heard the waitress say they were having a superbowl party which I am sure would be a blast. I got the jumbo burger and it had high quality meat with fresh veggies and a delicious bun. The special sauce tasted like it might have horseradish in it. The root beer was amazing and hand cut fried are very good. I ordered the hand apple pie to go and it was made to order and excellent. I would highly recites place.

    Wedge salad - half size
    Tina T.

    Overall this place is very interesting and the food is pretty good. I wanted something on the lighter end so I got the wedge salad (half size) but I couldn't finish it because there was way too much dressing. I was impressed they were able to get the dressing in between all the layers of the lettuce. This would be great for those who love extra dressing but it was just too heavy for me. But I did love the flavors overall and everything that was put into this dish. The soft boiled egg, the chives, bacon bits, pickled red onions, etc. It gave a slight Asian flavor to it, which I enjoyed, but again, just too much dressing for my personal liking. The restaurant was pretty big and had ample seating inside and out. There were a few flies hovering over the tables inside though which was a bit annoying.

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    2 years ago

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    1 year ago

    The chicken sandwich and the Greek ice cream with olive oil was delicious!! Definitely will be going again!

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    2 years ago

    Super cute and delicious food! Service was excellent. Will definitely be back with friends

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    2 years ago

    Good food, service (but can be slow), and prices, family friendly with a huge fenced yard off the back patio. A boon for the AV Valley.

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    2 years ago

    Everything here is absolutely fabulous. Food, service, atmosphere. Their sidewinder fries are to die for!!!

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    2 years ago

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    2 years ago

    Excellent. Clean, good food, great French fries, and outstanding service. And a nice selection of beer and wine.

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    2 years ago

    Great service, great lunch, efficient kitchen, responsive staff. We sat at outdoor tables. It was great.

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    2 years ago

    Amazing restaurant friendly staff and great food, would try again, the environment and decor is great too.

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    Page 4 of 4

    Ask the Community - Jumbo's Win Win

    Jumbo's Win Win - burgers - Updated June 2026

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